4-[1-(3-Cyano-5-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester → HCID 59394268, compound

HRID 45133Notes

Reaction equation

HRID 45133 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([O:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([C:28](=[O:42])[NH:29][C:30]3[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]#[N:41])[CH:31]=3)[CH:23]=[CH:22]4)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:40]([C:32]1[CH:31]=[C:30]([NH:29][C:28]([N:24]2[C:25]3[C:21](=[CH:20][C:19]([O:18][C:14]4[C:15]5[CH2:16][CH2:17][NH:8][CH2:9][C:10]=5[N:11]=[CH:12][N:13]=4)=[CH:27][CH:26]=3)[CH:22]=[CH:23]2)=[O:42])[CH:35]=[C:34]([C:36]([F:38])([F:39])[F:37])[CH:33]=1)#[N:41]

Participants

4

Reactant 1

HCID 675369894-[1-(3-Cyano-5-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester

Product 1

HCID 59394268HCID 59394268, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-[1-(3-cyano-5-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester (132 mg, 0.28 mmol) in DCM (2 mL) and TFA (2 mL) is stirred at room temperature for 2 h. The reaction is concentrated in vacuo and purified via semi-prep HPLC (C18; 10-100% I/H2O with 0.1% NH4OH) to give the title compound. MS (ESI) m/z 479.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.38-8.42 (m, 2 H), 8.35 (s, 1 H), 8.28 (d, J=8.8 Hz, 1 H), 8.07-8.12 (m, 2 H), 7.47 (d, J=2.3 Hz, 1 H), 7.14 (dd, J=8.8, 2.3 Hz, 1 H), 6.83 (d, J=3.3 Hz, 1 H), 3.85 (s, 2 H), 3.06 (t, J=5.8 Hz, 2 H), 2.74 (t, J=5.7 Hz, 2 H).

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. custompurified via semi-prep HPLC (C18; 10-100% I/H2O with 0.1% NH4OH)

Sources & evidence

ORD record
ord-8b78e6b6c04d4293b8c306bb42fcaaff
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

Loading…