Hydrochloric Acid → 3-(Cyclopropyl(2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)propanenitrile

HRID 1930658Notes

Reaction equation

[C:1]([CH2:3][CH2:4][N:5]([CH:36]1[CH2:38][CH2:37]1)[C:6]1[C:7]2[CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25][C:8]=2[N:9]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:23]=[CH:22][N:21]=[C:20]3[CH3:24])=[CH:15][CH:14]=2)[N:11]=1)#[N:2].Cl>CO>[CH:36]1([N:5]([C:6]2[C:7]3[CH2:28][NH:27][CH2:26][CH2:25][C:8]=3[N:9]=[C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH:23]=[CH:22][N:21]=[C:20]4[CH3:24])=[CH:15][CH:14]=3)[N:11]=2)[CH2:4][CH2:3][C:1]#[N:2])[CH2:37][CH2:38]1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-((2-cyanoethyl)(cyclopropyl)amino)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (240 mg, 0.47 mmol) was dissolved in methanol (5 mL). Hydrochloric acid (0.014 mL, 0.47 mmol) was added and the reaction mixture was stirred at 80° C. for 1 h. The solvent was evaporated under reduced pressure and the crude 3-(cyclopropyl(2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)propanenitrile (189 mg, 98%) was used as such in the subsequent step. MS (ES+) m/z 415.0 (M+H)+

Workup

customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-a4fc1fb688424adf87d7cffe91ebfb2c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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