Hydrochloric Acid → (S)-(1-(2-(4-(2-Methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol

HRID 1930642Notes

Reaction equation

HRID 1930642 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]1[C:12]1[C:13]2[CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31][C:14]=2[N:15]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][N:27]=[C:26]3[CH3:30])=[CH:21][CH:20]=2)[N:17]=1.Cl>CO>[CH3:30][C:26]1[N:25]([C:22]2[CH:23]=[CH:24][C:19]([NH:18][C:16]3[N:17]=[C:12]([N:4]4[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH2:11][C@H:3]4[CH2:2][OH:1])[C:13]4[CH2:34][NH:33][CH2:32][CH2:31][C:14]=4[N:15]=3)=[CH:20][CH:21]=2)[CH:29]=[CH:28][N:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59333813HCID 59333813, compound

Product 1

HCID 59333741(S)-(1-(2-(4-(2-Methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

(S)-tert-Butyl 4-(2-(hydroxymethyl)indolin-1-yl)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (65.3 mg, 0.12 mmol) was dissolved in methanol (3 mL). Hydrochloric acid (9.69 μL, 0.12 mmol) was added and the reaction mixture was stirred at 75° C. for 1 h. The solvent was evaporated under reduced pressure and the crude was used as such in the subsequent step. MS (ES+) m/z 454.3 (M+H)+

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d4dc7875522d4bae9e7c2b323c50dba8
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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