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Diisopropylethylamine → Tert-butyl 4-(4-(1-(di-tert-butoxyphosphoryloxy)-2-methylpropan-2-ylcarbamoyl)-2-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)phenylthio)phenylcarbamate

HRID 884016
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인쇄 미리보기

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HRID 884016 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][C:17]=2[NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[P:61]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])([O:63][CH2:64][C:65]([NH2:68])([CH3:67])[CH3:66])=[O:62].C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C>[C:70]([O:69][P:61]([O:63][CH2:64][C:65]([NH:68][C:20]([C:19]1[CH:23]=[CH:24][C:16]([S:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:14][CH:13]=2)=[C:17]([NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:37])[CH3:38])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)[CH:18]=1)=[O:21])([CH3:67])[CH3:66])([O:74][C:75]([CH3:77])([CH3:76])[CH3:78])=[O:62])([CH3:73])([CH3:72])[CH3:71]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 593768924-(4-tert-Butoxycarbonylamino-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acidHCID 866155662-Amino-2-methylpropyl di-tert-butyl phosphate

생성물 1

HCID 67041161
Tert-butyl 4-(4-(1-(di-tert-butoxyphosphoryloxy)-2-methylpropan-2-ylcarbamoyl)-2-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)phenylthio)phenylcarbamate
수율 62%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the product of Example 89E (100 mg, 0.19 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate [TBTU] (72 mg, 0.22 mmol), the product of Example 95C (65 mg, 0.23 mmol) in DMSO (1 mL) was added N,N-diisopropylethylamine (0.065 mL, 0.37 mmol) dropwise at room temperature under N2. The mixture was stirred at room temperature for 12 hours under N2. The reaction was diluted with ethyl acetate and the organic layer was washed sequentially with water (3×) and brine, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica gel, eluting with a gradient of ethyl acetate in dichloromethane (0-100%) to give the title compound (93 mg, 62%).

후처리

  1. washthe organic layer was washed sequentially with water (3×) and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel
  5. washeluting with a gradient of ethyl acetate in dichloromethane (0-100%)

출처 및 근거

ORD 기록
ord-3124aec104a34b44af94a7e004907223
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08236950B2

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