1-Methyl-1H-benzimidazol-6-amine → 4-[4-(3-Methyl-3H-benzimidazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 2375917Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21](Cl)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][N:25]1[C:29]2[CH:30]=[C:31]([NH2:34])[CH:32]=[CH:33][C:28]=2[N:27]=[CH:26]1>CCCCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:34][C:31]4[CH:32]=[CH:33][C:28]5[N:27]=[CH:26][N:25]([CH3:24])[C:29]=5[CH:30]=4)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (134 mg, 0.400 mmol) and 3-methyl-3H-benzoimidazol-5-ylamine (70.6 mg, 0.480 mmol) in n-BuOH (3 mL) in a sealed tube was heated at 120° C. for 17 h and concentrated in vacuo to obtain a brown solid that was purified using the mass-directed purification system to yield the title compound as beige solid. 1H NMR (CD3OD, 400 MHz): δ=1.52 (s, 9H), 2.57 (brs, 2H), 3.68 (brs, 2H), 3.93 (s, 3H), 4.12 (brs, 2H), 6.31 (brs, 1H), 6.65 (brs, 1H), 7.46 (dd, 1H, J=2.0 & 8.4 Hz), 7.66 (d, 1H, J=8.8 Hz), 8.14-8.15 (m, 2H), 8.23 (s, 1H), 8.24 (brs, 1H). MS (ES+): m/z 464.12 (100) [MH+]. HPLC: tR=2.18 min (ZQ2000, polar—5 min).

Workup

concentrationconcentrated in vacuo
customto obtain a brown solid that
customwas purified

Sources & evidence

ORD record: ord-cd91544cbd414287a00118f234367529
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465726B2

Reaction notes

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