Ammonium Hydroxide → 2-[(3aR,6R,6aS)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxy-methyl)-imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetamide

HRID 929224Notes

Reaction equation

HRID 929224 reaction equation
[OH-].[NH4+:2].[Cl:3][C:4]1[CH:5]=[C:6]2[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:23]([O:33][C@H:34]3[C@H:38]4[O:39][CH2:40][CH:41]([CH2:42][C:43]([O:45]CC)=O)[C@H:37]4[O:36][CH2:35]3)=[N:22][C:7]2=[N:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1>C(O)C>[Cl:3][C:4]1[CH:5]=[C:6]2[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:30])[CH3:32])[C:23]([O:33][C@H:34]3[C@H:38]4[O:39][CH2:40][CH:41]([CH2:42][C:43]([NH2:2])=[O:45])[C@H:37]4[O:36][CH2:35]3)=[N:22][C:7]2=[N:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 131735100HCID 131735100, compound

Product 1

HCID 1317350992-[(3aR,6R,6aS)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxy-methyl)-imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Concentrated ammonium hydroxide (0.15 mL) was added to a solution of ethyl 2-[(3aR,6R,6aS)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxymethyl)-imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetate (41.1 mg, 0.063 mmol) in ethanol (0.5 mL). The solution was stirred for 29 hours in a 50 degree oil bath. After cooling to room temperature, additional concentrated ammonium hydroxide (0.3 mL) was added and the mixture was heated for an additional 24 hours in a 50 degree oil bath. The solvents were removed under vacuum to give the title compound. C32H37ClN4O5Si 620.22 observed m/e: 621.38 (M+H)+ (Rt 0.98/2 min)

Workup

  1. temperaturethe mixture was heated for an additional 24 hours in a 50 degree oil bath
  2. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-3d629a4254754c2487a0cd16909f76f4
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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