Diisopropylethylamine → HCID 58293566, compound

HRID 1257927Notes

Reaction equation

HRID 1257927 reaction equation
C([N:4]([CH2:8][CH3:9])[CH:5](C)C)(C)C.[F:10][C:11]1[CH:27]=[C:26]([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:25]=[CH:24][C:12]=1[C:13]([NH:15][C@@H:16]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:17]([OH:19])=O)=[O:14].Cl.N1CCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[N:4]1([C:17]([C@@H:16]([NH:15][C:13](=[O:14])[C:12]2[CH:24]=[CH:25][C:26]([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)[CH2:38][CH2:39]5)=[CH:35][N:36]=4)[CH:33]=3)=[CH:27][C:11]=2[F:10])[C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH2:5][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 12308726Azetidine hydrochlorideHCID 67224992HCID 67224992, compound

Product 1

HCID 58293566HCID 58293566, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (14 μL, 0.084 mmol) was added to a mixture of (2S)-2-(2-fluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoylamino)-3,3-dimethylbutanoic acid (15 mg, 0.028 mmol), azetidine hydrochloride (3.9 mg 0.042 mmol), and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (18 mg, 0.042 mmol) in N,N-dimethylformamide (0.5 mL). After stirring at RT overnight, the reaction mixture was purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=577.2.

Workup

  1. customthe reaction mixture was purified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-13073061073e4911a8fd0889fd534fd7
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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