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

HRID 238119Notes

Reaction equation

HRID 238119 reaction equation
[Cl: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]>>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37][O:19][C:13]2[CH:12]=[C:11]3[C:16]([C:7]([NH:6][C:5]4[C:4]([F:23])=[CH:3][C:2]([Cl:1])=[CH:21][C:20]=4[F:22])=[N:8][CH:9]=[N:10]3)=[CH:15][C:14]=2[O:17][CH3:18])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

3

Reactant 2

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 1354968544-(4-Chloro-2,6-difluoroanilino)-7-hydroxy-6-methoxyquinazoline

Product 1

HCID 111352807-(1-(Tert-butoxycarbonyl)piperidin-4-ylmethoxy)-4-(4-chloro-2,6-difluoroanilino)-6-methoxyquinazolineYield 59%

Procedure

Using an analogous procedure to that described for the preparation of the starting material in Example 9, 4-(4-chloro-2,6-difluoroanilino)-7-hydroxy-6-methoxyquinazoline (150 mg, 0.44 mmol) was reacted with 1-(tert-butoxycarbonyl)-4-hydroxymethylpiperidine (150 mg, 0.88 mmol), (prepared as described for the starting material in Example 1), to give 7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-4-(4-chloro-2,6-difluoroanilino)-6-methoxyquinazoline (113 mg, 59%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-acff3872e2fa4613abb273d84b2587f7
Source dataset
uspto-grants-2014_02
Patent number
US08642608B2

Reaction notes

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