Diisopropylethylamine → HCID 58025679, compound

HRID 1694354Notes

Reaction equation

HRID 1694354 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]([C:13]3[C:14]([O:24][CH3:25])=[C:15]([CH:21]=[CH:22][CH:23]=3)[O:16][CH2:17][C:18](O)=[O:19])[N:10]([C:26](=[O:36])[C:27]3[C:32]([F:33])=[CH:31][C:30]([F:34])=[CH:29][C:28]=3[F:35])[N:9]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=[N:61][C:56]2[CH:57]=[CH:58][CH:59]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(NC)CC1>CN(C=O)C>[CH:57]1([CH2:56][NH:61][C:18](=[O:19])[CH2:17][O:16][C:15]2[CH:21]=[CH:22][CH:23]=[C:13]([CH:11]3[N:10]([C:26](=[O:36])[C:27]4[C:32]([F:33])=[CH:31][C:30]([F:34])=[CH:29][C:28]=4[F:35])[N:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[S:12]3)[C:14]=2[O:24][CH3:25])[CH2:59][CH2:58]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11029756N-MethylcyclopropanamineHCID 67279321HCID 67279321, compound

Product 1

HCID 58025679HCID 58025679, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of {3-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-acetic acid (0.029 mmol) in 1 mL of DMF is added DIEA (0.058 mmol), HATU (0.058 mmol) and cyclopropyl methylamine (0.058 mmol). The reaction mixture is stirred for 12 hours. The mixture is purified by preparative LC/MS (20-100% MeCN/H2O) to give N-cyclopropylmethyl-2-{3-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-acetamide: 1H NMR (400 MHz, CDCl3) δ 7.55-7.51 (m, 3H), 7.12-6.99 (m, 4H), 6.9 (d, J=7.6 Hz, 2H), 6.77 (t, J=8.4 Hz, 2H), 4.56 (s, 2H), 4.08 (s, 3H), 3.26-3.2 (m, 2H), 1.02-0.99 (m, 1H), 0.57-0.52 (m, 2H), 0.25 (m, 2H); LC/MS (ES+): 574.1 (M+1)+.

Workup

  1. customThe mixture is purified by preparative LC/MS (20-100% MeCN/H2O)

Sources & evidence

ORD record
ord-6e2796ae5206496b8525cfd3e8aab9b2
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

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