Diisopropylethylamine → HCID 66663334, compound

HRID 2190153Notes

Reaction equation

HRID 2190153 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:29][C:11]3=[N:12][C:13]([N:22]([CH2:27]C)[S:23]([CH3:26])(=[O:25])=[O:24])=[C:14]([CH2:16][CH2:17][CH2:18][C:19](O)=[O:20])[CH:15]=[C:10]3[C:9]=2[C:30](=[O:33])[NH:31][CH3:32])=[CH:4][CH:3]=1.[CH3:34][O:35][C:36]([C@@H:38]1[CH2:42][CH2:41][CH2:40][NH:39]1)=[O:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:29][C:11]3=[N:12][C:13]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:24])=[O:25])=[C:14]([CH2:16][CH2:17][CH2:18][C:19]([N:39]4[CH2:40][CH2:41][CH2:42][C@H:38]4[C:36]([O:35][CH3:34])=[O:37])=[O:20])[CH:15]=[C:10]3[C:9]=2[C:30](=[O:33])[NH:31][CH3:32])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 853477Methyl L-prolinateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66663685HCID 66663685, compound

Product 1

HCID 66663334HCID 66663334, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-ethylmethylsulfonamido)furo[2,3-b]pyridin-5-yl)butanoic acid (15 mg) in DMF (1 ml) is added (S)-methylpyrrolidine-2-carboxylate (4.2 mg), HATU (18.5 mg) and DIPEA (17 μl), and the mixture is stirred at rt for 30 min, and purified by preparative HPLC to afford the title compound. (M+H)+=575.2; Retention time=1.26 min, Method A. 1H NMR (400 MHz, CD3CN) δ ppm 8.18 (m, 1H), 8.06-8.01 (m, 2H), 7.33-7.26 (m, 2H), 6.91 (br s, 1H), 4.33-4.29 (m, 1H), 3.67 (s, 3H), 3.61-3.50 (m, 2H), 3.27 (s, 3H), 3.16 (s, 3H), 2.98-2.90 (m, 2H), 2.92 (d, 3H), 2.51-2.36 (m, 2H), 2.32-1.78 (m, 6H)

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-4ce48965edc94e3fa76fa7c8af12d94c
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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