Triethylamine → N-[2-amino-4-(6-iodo-1H-indazol-1-yl)pyrimidin-5-yl]-3-methyloxetane-3-carboxamide

HRID 1398495노트

반응식

HRID 1398495 반응식
[CH3:1][C:2]1([C:6]([OH:8])=O)[CH2:5][O:4][CH2:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[I:33][C:34]1[CH:42]=[C:41]2[C:37]([CH:38]=[N:39][N:40]2[C:43]2[C:48]([NH2:49])=[CH:47][N:46]=[C:45]([NH2:50])[N:44]=2)=[CH:36][CH:35]=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[NH2:50][C:45]1[N:44]=[C:43]([N:40]2[C:41]3[C:37](=[CH:36][CH:35]=[C:34]([I:33])[CH:42]=3)[CH:38]=[N:39]2)[C:48]([NH:49][C:6]([C:2]2([CH3:1])[CH2:5][O:4][CH2:3]2)=[O:8])=[CH:47][N:46]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 140289973-Methyl-3-oxetanecarboxylic AcidHCID 681817304-(6-iodo-1H-indazol-1-yl)pyrimidine-2,5-diamine

생성물 1

HCID 68181899N-[2-amino-4-(6-iodo-1H-indazol-1-yl)pyrimidin-5-yl]-3-methyloxetane-3-carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 3-methyloxetane-3-carboxylic acid (8.7 mg, 0.075 mmol) and HATU (28.5 mg, 0.075 mmol) was added a solution of crude 4-(6-iodo-1H-indazol-1-yl)pyrimidine-2,5-diamine (11% purity, 120 mg, 0.037 mmol) in DMF (0.5 mL) followed by triethylamine (0.016 mL, 0.112 mmol). The mixture was stirred at RT for 10 min, then diluted with EtOAc (10 mL) and washed with water (2×3 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give the crude compound. Purification by flash chromatography (Isolute column, 100% DCM to 3% MeOH in DCM) gave the title compound; m/z=+451.30 (M+H)+, (purity=76%). This intermediate was used in the next step without further purification.

후처리

  1. washwashed with water (2×3 mL)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give the crude compound
  6. customPurification by flash chromatography (Isolute column, 100% DCM to 3% MeOH in DCM)

출처 및 근거

ORD 기록
ord-de44690b126c4065b7772c219a60f29d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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