Ammonia → HCID 9869146, compound

HRID 454252Notes

Reaction equation

HRID 454252 reaction equation
C([O:4][C@H:5]([CH2:32][N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([O:18][C:19]3[C:20]([F:29])=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([CH3:28])=[CH:22]4)=[N:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:30][CH3:31])(=O)C.N>CO>[OH:4][C@H:5]([CH2:32][N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([O:18][C:19]3[C:20]([F:29])=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([CH3:28])=[CH:22]4)=[N:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:30][CH3:31]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54518398HCID 54518398, compound

Product 1

HCID 9869146HCID 9869146, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2R)-7-(2-acetoxy-3-(pyrrolidin-1-yl)propoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxyquinazoline (570 mg, 1.12 mmol) in methanol saturated with ammonia (7 ml) was stirred overnight at ambient temperature. The volatiles were removed under vacuum and the residue was purified by column chromatography eluting with methylene chloride/methanol containing ammonia (approximately 3N) to give (2R)-7-(2-hydroxy-3-(pyrrolidin-1-yl)propoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxyquinazoline (390 mg; 75%).

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe residue was purified by column chromatography
  3. washeluting with methylene chloride/methanol
  4. additioncontaining ammonia (approximately 3N)

Sources & evidence

ORD record
ord-a408b1f5534440df8b193d2264a8f703
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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