Dimethylformamide → HCID 67305476, 화합물

HRID 1010498노트

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HRID 1010498 반응식
[C:1]([O:5][C:6]([C@H:8]1[CH2:13][C:12]([F:15])([F:14])[CH2:11][NH:10][C@@H:9]1[C:16]([OH:18])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:20][C:21]1[CH:28]=[C:27]([C:29]2[CH2:30][CH2:31][NH:32][CH2:33][CH:34]=2)[CH:26]=[C:25]([CH3:35])[C:22]=1[C:23]#[N:24].CN(C)C=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>>[C:23]([C:22]1[C:25]([CH3:35])=[CH:26][C:27]([C:29]2[CH2:34][CH2:33][N:32]([C:16]([C@@H:9]3[C@@H:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][C:12]([F:14])([F:15])[CH2:11][NH:10]3)=[O:18])[CH2:31][CH:30]=2)=[CH:28][C:21]=1[CH3:20])#[N:24]

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67304512(2S,3S)-3-(tert-butoxycarbonyl)-5,5-difluoropiperidine-2-carboxylic AcidHCID 67305359HCID 67305359, 화합물

생성물 1

HCID 67305476HCID 67305476, 화합물

실험 절차

To a mixture of (2S,3S)-3-(tert-butoxycarbonyl)-5,5-difluoropiperidine-2-carboxylic acid (48 mg, 0.00018 mol) and 2,6-dimethyl-4-(1,2,3,6-tetrahydropyridin-4-yl)benzonitrile hydrochloride (84.7 mg, 0.000217 mol) TFA salt in N,N-dimethylformamide (0.406 mL, 0.00524 mol) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (96.0 mg, 0.000217 mol), followed by N,N-diisopropylethylamine (0.0756 mL, 0.000434 mol). The mixture was stirred at rt overnight, then quenched with aq. sodium bicarbonate. The mixture was extracted with EtOAc. The combined organic layers were washed with water, brine, dried, and evaporated to dry. The residue was used directly in next step without further purification. LCMS (M+H) 460.2.

후처리

  1. customquenched with aq. sodium bicarbonate
  2. extractionThe mixture was extracted with EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. customdried
  5. customevaporated
  6. customto dry
  7. customThe residue was used directly in next step without further purification

출처 및 근거

ORD 기록
ord-8d516efe8df9475f95bd56949ecafa73
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973041B2

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