Water → HCID 51356132, compound

HRID 2401230Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[CH:4][N:3]=1.[F:11][C:12]([F:25])([F:24])[C:13]1[NH:23][C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH2:22])[CH:20]=[C:15]2[CH:14]=1.CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1>[CH:8]1([C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:22][CH2:21][C:19]3[CH:20]=[C:15]4[CH:14]=[C:13]([C:12]([F:25])([F:24])[F:11])[NH:23][C:16]4=[N:17][CH:18]=3)[CH:7]=2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution of 4-chloro-6-cyclopropylpyrimidine (Intermediate 30, 75 mg, 0.485 mmol) in NMP (2 mL) in a 2 mL microwave vial was added and 1-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 104 mg, 0.485 mmol), DIPEA (0.169 mL, 0.970 mmol), vial de-gassed with argon and heated in a microwave at 120° C. for 2 hrs. The reaction mixture was poured into water (25 mL) and extracted with ethyl acetate (2×20 mL). The organic layers were combined, dried (MgSO4) and evaporated to dryness in vacuo to afford the crude residues. Resulting residues were then purified via MDAP. The appropriate fractions were collected, residue washed with methanol and evaporated to dryness in vacuo to give the title compound as a brown solid (40 mg).

Workup

extractionextracted with ethyl acetate (2×20 mL)
dry with materialdried (MgSO4)
customevaporated to dryness in vacuo
customto afford the crude residues
customResulting residues were then purified via MDAP
customThe appropriate fractions were collected
washresidue washed with methanol
customevaporated to dryness in vacuo

Sources & evidence

ORD record: ord-66ee3e12e9c84aa48989a4aab66fa9e8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796283B2

Reaction notes

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