Hydrochloric Acid → HCID 66877193, compound

HRID 871424Notes

Reaction equation

HRID 871424 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:45])[NH:12][C:13]2[CH:14]=[C:15]([CH:42]=[CH:43][CH:44]=2)[O:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:40][CH3:41])=[C:24]([O:27][C@H:28]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]4)[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:46].O1CCOCC1>>[ClH:46].[ClH:46].[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([NH:12][C:13]2[CH:44]=[CH:43][CH:42]=[C:15]([O:16][C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:40][CH3:41])=[C:24]([O:27][C@H:28]5[CH2:32][CH2:31][NH:30][CH2:29]5)[CH:25]=4)[N:20]=[CH:19][N:18]=3)[CH:14]=2)=[O:45])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 44243397HCID 44243397, compound

Product 1

HCID 66877193HCID 66877193, compoundYield 91%

Procedure

To a solution of (S)-tert-butyl 3-(4-(3-(3-(5-tert-butylisoxazole-3-yl)ureido)phenoxy)-7-methoxyquinazolin-6-yloxy)pyrrolidine-1-carboxylate (300 mg, ˜0.40 mmol), a 4N solution of HCl in dioxane (1 ml, 4 mmol) was added. The reaction mixture was stirred at room temperature overnight. The resulting solid was filtered and washed with plenty of ethyl ether to yield (S)-1-(5-tert-butylisoxazol-3-yl)-3-(3-(7-methoxy-6-(pyrrolidin-3-yloxy)quinazolin-4-yloxy)phenyl)urea dihydrochloride (215 mg, 91%). LC-MS (ESI) m/z 519 (M+H)+.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with plenty of ethyl ether

Sources & evidence

ORD record
ord-890aa94c293e4a6eaddcb554cca0d116
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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