1-Methylimidazole → HCID 66549331, compound

HRID 1410070Notes

Reaction equation

HRID 1410070 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:8]=[C:9]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=3)[C:10]3[N:15]=[CH:14][S:13][C:11]=3[N:12]=2)[CH2:3]1.[NH:27]1[C:35]2[C:30](=[CH:31][C:32]([C:36](O)=[O:37])=[CH:33][CH:34]=2)[CH:29]=[N:28]1.CN1C=CN=C1.CCN=C=NCCCN(C)C>ClCCl>[CH3:26][O:25][C:19]1[CH:18]=[C:17]([NH:16][C:9]2[C:10]3[N:15]=[CH:14][S:13][C:11]=3[N:12]=[C:7]([N:4]3[CH2:5][CH2:6][CH:2]([NH:1][C:36]([C:32]4[CH:31]=[C:30]5[C:35](=[CH:34][CH:33]=4)[NH:27][N:28]=[CH:29]5)=[O:37])[CH2:3]3)[N:8]=2)[CH:22]=[CH:21][C:20]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 42484541H-Indazole-5-carboxylic acidHCID 68379272HCID 68379272, compound

Product 1

HCID 66549331HCID 66549331, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (100 mg, 0.27 mmol) and 1H-indazole-5-carboxylic acid (44 mg, 0.27 mmol) in dichloromethane (20 mL) were added the solution of 1-methyl-1H-imidazole (88 mg, 1.1 mmol) and EDCI (206 mg, 1.1 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 15 hours, the solid formed during the reaction was collected by filtration and washed with MeOH to afford N-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-1H-indazole-5-carboxamide (78 mg, 56.1%) as a off-white solid. 1H NMR (300 MHz, DMSO): δ 13.25 (s, 1H), 9.58 (s, 1H), 8.81 (s, 1H), 8.61 (d, 1H, J=6.3 Hz), 8.36 (s, 1H), 8.19 (s, 1H), 7.88-7.86 (m, 2H), 7.56 (d, 1H, J=8.7 Hz), 7.50 (s, 1H), 6.91 (d, 1H, J=8.4 Hz), 4.61-4.59 (m, 1H), 3.73 (s, 3H), 3.65 (s, 3H), 3.62 (brs, 3H), 2.28-2.09 (m, 2H). LC-MS: 517 [M+H]+, tR=1.34 min. HPLC: 95.89% at 214 nm, 97.39% at 254 nm, tR=4.52 min

Workup

  1. customthe solid formed during the reaction
  2. filtrationwas collected by filtration
  3. washwashed with MeOH

Sources & evidence

ORD record
ord-0bd61c9f8d4d48f8bdab255788c0cbba
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

Loading…