1-Methylimidazole → HCID 66549517, compound

HRID 1410075Notes

Reaction equation

HRID 1410075 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.[CH3:27][O:28][C:29]([C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][N:32]=1)=[O:30].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:35]([C:34]4[CH:38]=[CH:39][C:31]([C:29]([O:28][CH3:27])=[O:30])=[N:32][CH:33]=4)=[O:36])[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 5796316-(Methoxycarbonyl)pyridine-3-carboxylic acidHCID 68379272HCID 68379272, compound

Product 1

HCID 66549517HCID 66549517, compoundYield 80.3%

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 (80 mg, 0.22 mmol) and 6-(methoxycarbonyl)nicotinic acid (39 mg, 0.22 mmol) in dichloromethane (15 mL) was added the solution of 1-methyl-1H-imidazole (71 mg, 0.88 mmol) and EDCI (164 mg, 0.88 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 15 hours, the solid was collected by filtration and washed with MeOH to afford methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)picolinate (90 mg, 80.3%) as a off-white solid. 1H NMR (300 MHz, DMSO): δ 9.57 (s, 1H), 9.07 (s, 1H), 8.99 (d, 1H, J=6.3 Hz), 8.79 (s, 1H), 8.36 (dd, 1H, J1=8.1 Hz, J2=2.1 Hz), 8.11 (d, 1H, J=8.1 Hz), 7.86 (s, 1H), 7.45 (s, 1H), 6.90 (d, 1H, J=8.7 Hz), 4.60-4.58 (m, 1H), 3.89 (s, 3H), 3.75 (s, 3H), 3.71 (s, 3H), 3.64 (brs, 4H), 2.28-2.24 (m, 1H), 2.11-2.06 (m, 1H). LC-MS: 536 [M+H]+, tR=1.37 min. HPLC: 95.95% at 214 nm, 96.44% at 254 nm, tR=4.85 min.

Workup

  1. filtrationthe solid was collected by filtration
  2. washwashed with MeOH

Sources & evidence

ORD record
ord-953d055eb0b8417891a5fc53bac91455
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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