Triethylamine → HCID 59505148, compound

HRID 1672063Notes

Reaction equation

HRID 1672063 reaction equation
[F:1][C:2]1[C:7]2[C:8]([C:18](=[O:21])[NH:19][CH3:20])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[CH3:31])[C:25]([OH:27])=O.[CH3:32][C:33]1[CH:38]=[C:37]([CH3:39])[N:36]=[C:35]([C:40]2([NH2:43])[CH2:42][CH2:41]2)[N:34]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[CH3:39][C:37]1[CH:38]=[C:33]([CH3:32])[N:34]=[C:35]([C:40]2([NH:43][C:25]([C:24]3[CH:28]=[CH:29][C:30]([CH3:31])=[C:22]([C:3]4[CH:4]=[CH:5][C:6]5[O:10][C:9]([C:11]6[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=6)=[C:8]([C:18]([NH:19][CH3:20])=[O:21])[C:7]=5[C:2]=4[F:1])[CH:23]=3)=[O:27])[CH2:41][CH2:42]2)[N:36]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 552956881-(4,6-Dimethyl-2-pyrimidinyl)cyclopropanamineHCID 592756803-(4-Fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acid

Product 1

HCID 59505148HCID 59505148, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acid (50 mg, 0.12 mmol), crude 1-(4,6-dimethylpyrimidin-2-yl)cyclopropanamine (150 mg) in 2 ml DMF at room temperature was added BOP (106 mg, 0.24 mmol, 2.0 eq.) and triethyl amine (0.050 ml, 0.36 mmol, 3.0 eq.), and the mixture stirred overnight under an N2 atmosphere. The mixture was poured into crushed ice, and solid precipitate was filtered and dried. The product obtained was further purified by column chromatography using Silica gel (230-400) and CHCl3-MeOH (95:5) as a mobile phase. Yield: 40 mg (60%). 1H NMR (400 MHz, CDCl3): δ 8.00-7.97 (m, 2H), 7.80-7.76 (m, 2H), 7.41-7.37 (m, 3H), 7.21-7.15 (m, 3H), 6.77 (s, 1H), 6.22 (br. s., 1H), 3.01 (d, J=5.0 Hz, 3H), 2.37 (s, 6H), 2.26 (s, 3H), 1.76-1.73 (m, 2H), 1.56-1.54 (m, 2H). 19F NMR (376.57 MHz, CDCl3): δ−109.83, −119.22 LCMS: (ES+) m/z=567.2 (M+H)+

Workup

  1. additionThe mixture was poured
  2. custominto crushed ice, and solid precipitate
  3. filtrationwas filtered
  4. customdried
  5. customThe product obtained
  6. customwas further purified by column chromatography

Sources & evidence

ORD record
ord-cc25d1afe25a426e8eba1e21e5389858
Source dataset
uspto-grants-2011_08
Patent number
US07994171B2

Reaction notes

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