Triethylamine → HCID 58972567, compound

HRID 1485360Notes

Reaction equation

HRID 1485360 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[C:5]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[C:6]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[N:13]=1.[CH3:25][O:26][C:27](=[O:36])[C:28]1[CH:33]=[C:32]([Cl:34])[C:31](Cl)=[N:30][CH:29]=1.CCN(CC)CC>CN(C=O)C.O>[Cl:34][C:32]1[CH:33]=[C:28]([C:27]([O:26][CH3:25])=[O:36])[CH:29]=[N:30][C:31]=1[N:10]1[CH2:11][CH2:12][C:6]2[C:5]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:17][CH:16]=3)=[N:4][C:3]([S:2][CH3:1])=[N:13][C:7]=2[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2782166Methyl 5,6-DichloronicotinateHCID 68949280HCID 68949280, compound

Product 1

HCID 58972567HCID 58972567, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (2-methylsulfanyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl)-(4-trifluoromethyl-phenyl)-amine (187 mg, 0.53 mmol), 5,6-dichloro-nicotinic acid methyl ester (129 mg, 0.58 mmol), and Et3N (0.2 mL, 1.58 mmol) in DMF (1.2 mL) was heated at 120° C. for 2 h. The mixture was cooled to rt, diluted with water, and extracted with EtOAc. The combined organic layers were dried and concentrated. The residue was purified (FCC) to give the title compound (203 mg, 74%). MS (ESI): mass calcd. for C23H21ClF3N5O2S, 523.11; m/z found, 524.1 [M+H]+. 1H NMR (CDCl3): 8.57 (d, J=2.0 Hz, 1H), 8.00 (d, J=2.0 Hz, 1H), 7.59 (d, J=8.6 Hz, 2H), 7.48 (d, J=8.6 Hz, 2H), 6.73-6.59 (m, 1H), 3.89-3.65 (m, 7H), 3.19-3.07 (m, 2H), 2.95-2.87 (m, 2H), 2.40 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customThe residue was purified (FCC)

Sources & evidence

ORD record
ord-cfac17c2f50a4df8b6f4f5a15e4c5b41
Source dataset
uspto-grants-2016_08
Patent number
US09422293B2

Reaction notes

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