Diisopropylethylamine → 4-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-3-methoxy-N-(4-pyrrolidin-1-ylcyclohexyl)benzamide

HRID 2234317노트

반응식

HRID 2234317 반응식
[CH:1]1([N:6]2[CH2:16][C:15]([CH3:18])([CH3:17])[C:14](=[O:19])[N:13]([CH3:20])[C:12]3[C:7]2=[N:8][C:9]([NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][C:23]=2[O:31][CH3:32])=[N:10][CH:11]=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:33]1([CH:38]2[CH2:43][CH2:42][CH:41]([NH2:44])[CH2:40][CH2:39]2)[CH2:37][CH2:36][CH2:35][CH2:34]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:1]1([N:6]2[CH2:16][C:15]([CH3:17])([CH3:18])[C:14](=[O:19])[N:13]([CH3:20])[C:12]3[C:7]2=[N:8][C:9]([NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([NH:44][CH:41]4[CH2:40][CH2:39][CH:38]([N:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)[CH2:43][CH2:42]4)=[O:28])=[CH:24][C:23]=2[O:31][CH3:32])=[N:10][CH:11]=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21882596Cyclohexanamine, 4-(1-pyrrolidinyl)-, trans-(9CI)2회HCID 426107874-(9-cyclopentyl-5,7,7-trimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid2회

생성물 1

HCID 581539494-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-3-methoxy-N-(4-pyrrolidin-1-ylcyclohexyl)benzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-3-methoxy-benzoic acid (Intermediate 236; 83 mg, 0.19 mmol) in DMF (3 mL) was added a solution of 4-pyrrolidin-1-ylcyclohexan-1-amine (Intermediate 237; 78 mg, 0.46 mmol). DIPEA (100 uL, 0.57 mmol) was added, followed by HATU (107 mg, 0.28 mmol). The resultant mixture was stirred at ambient temperature for 2 hours. The reaction mixture was evaporated to a gum, which was partitioned between DCM (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL). The organic phase was separated by gravity elution through a PTFE filter cup and evaporated to an amber gum which was purified by base modified reverse phase preparative HPLC to yield the title compound as an off white solid (34 mg, 30%).

후처리

  1. customThe reaction mixture was evaporated to a gum, which
  2. customwas partitioned between DCM (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL)
  3. customThe organic phase was separated by gravity elution through a PTFE
  4. filtrationfilter cup
  5. customevaporated to an amber gum which
  6. customwas purified by base modified reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-9c9b03c6ca4047c1bdc41ef047b160e9
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709471B2

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