Water → HCID 178483042, 화합물

HRID 81269노트

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HRID 81269 반응식
Cl.[CH3:2][NH:3][CH3:4].C(=O)(O)[O-].[Na+].O.[Cl:11][C:12]1[N:17]=[C:16]([C:18]2[C:19](F)=[N:20][CH:21]=[C:22]([Cl:24])[CH:23]=2)[C:15]2[N:26]([CH2:38][C@H:39]3[CH2:44][CH2:43][C@H:42]([CH3:45])[CH2:41][CH2:40]3)[C:27]([N:29]3[CH2:34][CH2:33][O:32][C@@H:31]4[CH2:35][CH2:36][CH2:37][C@@H:30]34)=[N:28][C:14]=2[CH:13]=1>CCO>[Cl:24][C:22]1[CH:23]=[C:18]([C:16]2[C:15]3[N:26]([CH2:38][C@H:39]4[CH2:44][CH2:43][C@H:42]([CH3:45])[CH2:41][CH2:40]4)[C:27]([N:29]4[CH2:34][CH2:33][O:32][C@@H:31]5[CH2:35][CH2:36][CH2:37][C@@H:30]45)=[N:28][C:14]=3[CH:13]=[C:12]([Cl:11])[N:17]=2)[C:19]([N:3]([CH3:4])[CH3:2])=[N:20][CH:21]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 516892Sodium BicarbonateHCID 178461232HCID 178461232, 화합물

생성물 1

HCID 178483042HCID 178483042, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
90 °C

실험 절차

To a solution of dimethylamine hydrochloride (580 mg, 7.25 mmol) and sodium bicarbonate (812 mg, 9.67 mmol) in EtOH:water (4 mL:2 mL) was added 6-chloro-4-(5-chloro-2-fluoropyridin-3-yl)-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (racemic) (125 mg, 0.24 mmol). The reaction was heated to 90° C. for 5 hours. The reaction was then concentrated and diluted with EtOAc. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification of the residue on a silica gel column (0 to 45% EtOAc/hexanes) afforded 5-chloro-3-{6-chloro-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-4-yl}-N,N-dimethylpyridin-2-amine (racemic). MS ES calc'd. for C28H36Cl2N6O [M+H]+ 543. found 543.

후처리

  1. concentrationThe reaction was then concentrated
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue on a silica gel column (0 to 45% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-50523daab8b14110af457642bf86ef67
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846657B2

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