(5-Amino-2H-pyrazol-3-yl)-acetic acid → {3-[(7-{[(2R)-1-(2-tert-butoxyethyl)pyrrolidin-2-yl]methoxy}-6-methoxyquinazolin-4-yl)amino]-1H-pyrazol-5-yl}acetic acid

HRID 749176Notes

Reaction equation

HRID 749176 reaction equation
[C:1]([O:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[C:16]([O:28][CH3:29])=[CH:17][C:18]([C:26]#[N:27])=[C:19]([N:21]=[CH:22]N(C)C)[CH:20]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:30][C:31]1[CH:35]=[C:34]([CH2:36][C:37]([OH:39])=[O:38])[NH:33][N:32]=1>C(O)(=O)C>[C:1]([O:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[C:19]2[C:18]([C:26]([NH:30][C:31]3[CH:35]=[C:34]([CH2:36][C:37]([OH:39])=[O:38])[NH:33][N:32]=3)=[N:27][CH:22]=[N:21]2)=[CH:17][C:16]=1[O:28][CH3:29])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 16221512(5-Amino-2H-pyrazol-3-yl)-acetic acidHCID 68989803N'-(5-{[(2R)-1-(2-tert-butoxyethyl)pyrrolidin-2-yl]methoxy}-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide

Product 1

HCID 68987483{3-[(7-{[(2R)-1-(2-tert-butoxyethyl)pyrrolidin-2-yl]methoxy}-6-methoxyquinazolin-4-yl)amino]-1H-pyrazol-5-yl}acetic acidYield 49.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N′-(5-{[(2R)-1-(2-tert-butoxyethyl)pyrrolidin-2-yl]methoxy}-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide (300 mg, 0.74 mmol) in acetic acid (0.64 ml) was reacted with (3-amino-1H-pyrazol-5-yl)acetic acid (110 mg, 0.78 mmol) at 120° C. for 20 minutes. The solvent was evaporated, and the residue triturated with dichloromethane to yield {3-[(7-{[(2R)-1-(2-tert-butoxyethyl)pyrrolidin-2-yl]methoxy}-6-methoxyquinazolin-4-yl)amino]-1H-pyrazol-5-yl}acetic acid (183 mg, 47% yield):

Workup

  1. customThe solvent was evaporated
  2. customthe residue triturated with dichloromethane

Sources & evidence

ORD record
ord-c6eabe039c704e93ac128db8de436d08
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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