Hydrochloric Acid → 2-[5-Chloro-2-(1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-5-piperidin-1-yl-benzamide

HRID 1040842노트

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HRID 1040842 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])[C:5]([Cl:24])=[CH:4][N:3]=1.[NH2:25][C:26]1[CH:38]=[CH:37][C:29]2[N:30]([CH3:36])[C:31](=[O:35])[CH2:32][CH2:33][CH2:34][C:28]=2[CH:27]=1.Cl>COC(O)C.O1CCOCC1>[Cl:24][C:5]1[C:6]([NH:8][C:9]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])=[N:7][C:2]([NH:25][C:26]2[CH:38]=[CH:37][C:29]3[N:30]([CH3:36])[C:31](=[O:35])[CH2:32][CH2:33][CH2:34][C:28]=3[CH:27]=2)=[N:3][CH:4]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 197602587-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[B]azepin-2-oneHCID 866338852-(2,5-Dichloro-pyrimidin-4-ylamino)-5-piperidin-1-yl-benzamide

생성물 1

HCID 668299562-[5-Chloro-2-(1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-5-piperidin-1-yl-benzamide수율 21.1%

시약·촉매·용매 2

HCID 312751,4-Dioxane용매HCID 30156371-Methoxyethanol용매

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온도
120 °C

실험 절차

2-(2,5-dichloro-pyrimidin-4-ylamino)-5-piperidin-1-yl-benzamide (50.1 mg, 0.137 mmol) and 7-amino-1-methyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (28.7 mg, 0.151 mmol) were slurried in methoxyethanol (2.0 mL) prior to adding ˜0.2 mL of 4N HCl in dioxane. This mixture was heated at 120° C. for 2 h. After quenching with saturated aqueous NaHCO3 solution (2 mL), the resulting precipitate was collected by filtration, successively washed water (5×2 mL) and ether (2×1 mL) to afford product (15 mg, 21%) as a yellow powder that had the following properties: mp: 295-297° C.; LC/MS (ESI+): 520 (M+H); 1H-NMR (DMSO-d6, 400 MHz): δ 11.20 (s, 1H), 9.45 (s, 1H), 8.42 (d, J=8.0, 1H), 8.28 (s, 1H), 8.15 (s, 1H), 7.65 (m, 2H), 7.52 (d, J=8.9, 1H), 7.30 (s, 1H), 7.20 (d, J=8.6, 1H), 7.05 (d, J=9.4, 1H), 3.20 (s, 3H), 3.18 (m, 4H), 2.65-2.20 (series of m, 6H), 1.65 (m, 4H), 1.55 (m, 2H).

후처리

  1. customAfter quenching with saturated aqueous NaHCO3 solution (2 mL)
  2. filtrationthe resulting precipitate was collected by filtration, successively washed water (5×2 mL) and ether (2×1 mL)

출처 및 근거

ORD 기록
ord-dea069d8f4c84dc988f97eb11d805544
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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