Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → 4-(4-Bromo-2,6-difluoroanilino)-7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-6-methoxyquinazoline

HRID 238115Notes

Reaction equation

HRID 238115 reaction equation
[Br:1][C:2]1[CH:21]=[C:20]([F:22])[C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:23])[CH:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37]O)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[Br:1][C:2]1[CH:3]=[C:4]([F:23])[C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:37][CH:34]4[CH2:35][CH2:36][N:31]([C:29]([O:28][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:30])[CH2:32][CH2:33]4)=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:20]([F:22])[CH:21]=1

Participants

3

Reactant 2

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 1354935444-(4-Bromo-2,6-difluoroanilino)-7-hydroxy-6-methoxyquinazoline

Product 1

HCID 109738974-(4-Bromo-2,6-difluoroanilino)-7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-6-methoxyquinazolineYield 41%

Procedure

Using an analogous procedure to that described in the preparation of the starting material in Example 8, 4-(4-bromo-2,6-difluoroanilino)-7-hydroxy-6-methoxyquinazoline (1 g, 2.62 mmol) was reacted with 1-(tert-butoxycarbonyl)-4-hydroxymethylpiperidine (845 mg, 3.93 mmol), (prepared as described for the starting material in Example 1), to give 4-(4-bromo-2,6-difluoroanilino)-7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-6-methoxyquinazoline (620 mg, 41%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-7405efded057413aafc63145250572dd
Source dataset
uspto-grants-2014_02
Patent number
US08642608B2

Reaction notes

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