(5-Amino-2H-pyrazol-3-yl)-acetic acid → (3-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-5-yl)acetic acid hydrochloride

HRID 1864478Notes

Reaction equation

HRID 1864478 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:17][C:18]1[CH:22]=[C:21]([CH2:23][C:24]([OH:26])=[O:25])[NH:20][N:19]=1>CN1CCCC1=O>[ClH:1].[Cl:16][CH2:15][CH2:14][CH2:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:17][C:18]3[CH:22]=[C:21]([CH2:23][C:24]([OH:26])=[O:25])[NH:20][N:19]=3)=[N:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 16221512(5-Amino-2H-pyrazol-3-yl)-acetic acidHCID 162215144-Chloro-7-(3-chloropropoxy)quinazoline

Product 1

HCID 67000008(3-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-5-yl)acetic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-Chloro-7-(3-chloropropoxy)quinazoline was added to 1 molar equivalent of a solution of (3-amino-1H-pyrazol-5-yl)acetic acid in N-methylpyrrolidinone (NMP) and then left for a period of 12 hours. Crystallisation of the product was observed to occur with and without seeding and with and without the addition of acetonitrile as an anti-solvent. The resultant solid was isolated by filtration, washed with N-methylpyrrolidinone and acetonitrile and then dried in vacuo to yield (3-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-5-yl)acetic acid.hydrochloride as an off-white solid:

Workup

  1. customCrystallisation of the product
  2. additionwith and without the addition of acetonitrile as an anti-solvent
  3. customThe resultant solid was isolated by filtration
  4. washwashed with N-methylpyrrolidinone and acetonitrile
  5. customdried in vacuo

Sources & evidence

ORD record
ord-cecf00fcc7cb469597e4ee4f40448be9
Source dataset
uspto-grants-2009_12
Patent number
US07625910B2

Reaction notes

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