Diisopropylethylamine → HCID 178461793, compound

HRID 1437828Notes

Reaction equation

HRID 1437828 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]2[NH:7][C:8]3[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:9]=3[N:10]=2)[N:3]=[CH:2]1.[OH:16][C@:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:21])[C:18]([OH:20])=[O:19].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C)C=O>[OH:16][C@:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:21])[C:18]([NH:15][C:13]1[CH:12]=[CH:11][C:9]2[NH:10][C:6]([C:4]3[N:3]=[CH:2][S:1][CH:5]=3)=[N:7][C:8]=2[CH:14]=1)=[O:19].[C:22]1([C@H:17]([CH3:21])[C:18]([NH:15][C:13]2[CH:12]=[CH:11][C:9]3[NH:10][C:6]([C:4]4[N:3]=[CH:2][S:1][CH:5]=4)=[N:7][C:8]=3[CH:14]=2)=[O:20])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1349122-(1,3-Thiazol-4-yl)-1H-benzimidazol-6-amineHCID 445144(S)-Atrolactic acidHCID 2724699PyBOP

Product 2

HCID 178461793HCID 178461793, compoundHCID 178473425HCID 178473425, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-thiazol-4-yl-3H-benzoimidazol-5-ylamine (1-6, 103 mg, 0.476 mmol), (2S)-2-Hydroxy-2-phenyl-propionic acid (79 mg, 0.48 mmol) and diisopropylethylamine (0.166 mL, 0.95 mmol) in N,N-dimethylformamide (5 mL) was reacted at the ambient temperature with benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBop, 273 mg, 0.52 mmol). After 3 h stirring at the same temperature, the reaction mixture was concentrated under the reduced pressure and the residue was partitioned between ethyl acetate (50 mL) and aqueous sodium bicarbonate solution (40 mL). The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. The resulting crude product was triturated with ethyl acetate (3 mL), collected by filtration, and dried under the reduced pressure to afford (2S)-2-Hydroxy-2-phenyl-N-[2-(1,3-thiazol-4-yl)-1H-benzimidazol-5-yl]propanamide as a white solid (3-62); 1H NMR (500 MHz, DMSO-d6) δ 12.88 (s, 1H), 9.72 (s, 1H), 9.31 (s, 1H), 8.42 (s, 1H), 8.12 (s, 1H), 7.65 (d, 2H, J=8.5 Hz), 7.52 (m, 1H), 7.36 (m, 3H), 7.26 (m, 1H), 6.45 (s, 1H), 1.72 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under the reduced pressure
  2. customthe residue was partitioned between ethyl acetate (50 mL) and aqueous sodium bicarbonate solution (40 mL)
  3. washThe organic layer was washed with brine
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was triturated with ethyl acetate (3 mL)
  8. filtrationcollected by filtration
  9. customdried under the reduced pressure

Sources & evidence

ORD record
ord-2126b64e9b884c6a9eb34d15180945ca
Source dataset
uspto-grants-2009_11
Patent number
US07622592B2

Reaction notes

Loading…