Diisopropylethylamine → HCID 25144677, compound

HRID 500180Notes

Reaction equation

HRID 500180 reaction equation
C([N:4]([CH2:8][CH3:9])[CH:5](C)C)(C)C.Cl.Cl.Cl.[CH3:13][C:14]([CH3:51])([CH3:50])[C@H:15]([NH:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:29]=[N:30][C:31]3[N:32]([C:34]([C:37]4([C:40]5[CH:41]=[C:42]6[C:47](=[CH:48][CH:49]=5)[N:46]=[CH:45][CH:44]=[CH:43]6)[CH2:39][CH2:38]4)=[CH:35][N:36]=3)[CH:33]=2)=[CH:24][N:23]=1)=[O:21])[C:16](O)=[O:17].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.N1CCC1>CN(C)C=O.CO>[N:4]1([C:16]([C@@H:15]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:29]=[N:30][C:31]4[N:32]([C:34]([C:37]5([C:40]6[CH:41]=[C:42]7[C:47](=[CH:48][CH:49]=6)[N:46]=[CH:45][CH:44]=[CH:43]7)[CH2:39][CH2:38]5)=[CH:35][N:36]=4)[CH:33]=3)=[CH:24][N:23]=2)=[O:21])[C:14]([CH3:50])([CH3:13])[CH3:51])=[O:17])[CH2:5][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 12308726Azetidine hydrochlorideHCID 67224121HCID 67224121, compound

Product 1

HCID 25144677HCID 25144677, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (30 μL, 0.172 mmol) was added to a mixture of (2S)-3,3-dimethyl-2-[(5-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]pyridin-2-ylcarbonyl)amino]butanoic acid trihydrochloride (16.4 mg, 0.026 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (12.6 mg, 0.0286 mmol) and azetidine hydrochloride (3.65 mg, 0.039 mmol) in N,N-dimethylformamide (1.0 mL). The mixture was stirred at RT for 3 h, and was diluted with methanol (0.8 mL). The resulting solution was purified by RP-HPLC (pH 10) to give the desired product. LCMS: (M+H)=560.2.

Workup

  1. customThe resulting solution was purified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-5301c78477064a9aa63ce9d4e0423ea7
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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