1,1'-Carbonyldiimidazole → HCID 178422188, compound

HRID 884547

Reaction equation

HRID 884547 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:17]([CH3:18])[CH2:16][C:15]2[C:14]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][CH:24]=[CH:23]4)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:34]([N:36]2[CH:40]=[N:39]C=C2)=[O:35])C=1.[C:41]([C:45]1[CH:46]=C(N)N[N:49]=1)([CH3:44])([CH3:43])[CH3:42].N1(C2C=CN=CC=2)CCCC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:17]([CH3:18])[CH2:16][C:15]2[C:14]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[N:25]([C:34](=[O:35])[NH:36][C:40]3[NH:39][N:49]=[C:45]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:46]=3)[CH:24]=[CH:23]4)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 755674-PyrrolidinopyridineHCID 593941184-(1H-indol-5-yloxy)-6-methyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl esterHCID 178441179HCID 178441179, compound

Product 1

HCID 178422188HCID 178422188, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(1H-indol-5-yloxy)-6-methyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester (210 mg, 0.55 mmol), CDI (179 mg, 1.10 mmol), TEA (230 uL, 1.65 mmol), and DMF (5 mL) is stirred at rt 1 h before 5-tert-butyl-2H-pyrazol-3-ylamine (77 mg, 0.55 mmol) and 4-pyrrolidinopyridine (16.4 mg, 0.11 mmol) are added. After 24 h, the reaction is concentrated in vacuo and the purified via FCC (5-90% EtOAc/heptane) to give the title compound. MS (ESI) m/z 546.3 (M+1).

Workup

  1. additionare added
  2. concentrationthe reaction is concentrated in vacuo
  3. customthe purified via FCC (5-90% EtOAc/heptane)

Sources & evidence

ORD record
ord-534fcbc33d594f68bccc8c8d48906bda
Source dataset
uspto-grants-2012_08
Patent number
US08242125B2

Linked notes

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