Diisopropylethylamine → HCID 57925919, compound

HRID 1013479Notes

Reaction equation

HRID 1013479 reaction equation
[CH3:1][O:2][P:3]([C:7]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)([F:9])[CH3:8])([O:5][CH3:6])=[O:4].C(OC(=O)[NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)=[CH:28][C:27]=1[NH2:37])(C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:6][O:5][P:3]([C:7]([C:10]1[CH:11]=[CH:12][C:13]([C:14](=[O:16])[NH:37][C:27]2[CH:28]=[C:29]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[CH:30]=[CH:31][C:26]=2[NH2:25])=[CH:17][CH:18]=1)([F:9])[CH3:8])(=[O:4])[O:2][CH3:1]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamateHCID 57925897HCID 57925897, compound

Product 1

HCID 57925919HCID 57925919, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[1-(Dimethoxy-phosphoryl)-1-fluoro-ethyl]-benzoic acid (50 mg, 0.18 mmol), (2-Amino-4-thiophen-2-yl-phenyl)-carbamic acid tert-butyl ester (63 mg, 0.22 mmol), BOP (96 mg, 0.22 mmol), and DIPEA (70 mg, 0.54 mmol) were combined and diluted with DMF (0.72 mL). The resulting mixture was stirred at ambient temperature for 18 hours. The reaction mixture was purified directly by HPLC (20-85% MeCN in water w/0.025% TFA). Pure fractions were identified, combined, and concentrated in vacuo. The residue was diluted with 5:1 CH2Cl2:TFA. The resulting solution was stirred at ambient temperature for 1 h then concentrated in vacuo to afford the title compound: 1H NMR (DMSO-d6, 600 MHz) 10.15 (s, 1H), 8.05 (d, J=9.0 Hz, 2H), 7.56-7.62 (m, 3H), 7.43-7.48 (m, 2H), 7.37 (d, J=3.5 Hz, 1H), 7.06-7.09 (m, 2H), 3.72 (d, J=10.8 Hz, 3H), 3.57 (d, J=10.8 Hz, 3H), 1.86-1.96 (m, 3H). MS: cal'd 449 (MH+), exp 449 (MH+)

Workup

  1. customThe reaction mixture was purified directly by HPLC (20-85% MeCN in water w/0.025% TFA)
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with 5:1 CH2Cl2
  4. stirringThe resulting solution was stirred at ambient temperature for 1 h
  5. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-296c7204697a4e06ab3fa5919cbcf5a5
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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