Morpholine → HCID 178519836, compound

HRID 707368Notes

Reaction equation

HRID 707368 reaction equation
[CH:1]1([N:4]2[C:12]3[C:7](=[N:8][CH:9]=[CH:10][N:11]=3)[N:6]([C@H:13]3[CH2:16][C@H:15]([NH:17][C:18]4[S:19][C:20]([C:23]([OH:25])=O)=[CH:21][N:22]=4)[CH2:14]3)[C:5]2=[O:26])[CH2:3][CH2:2]1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>>[CH:1]1([N:4]2[C:12]3=[N:11][CH:10]=[CH:9][N:8]=[C:7]3[N:6]([C@H:13]3[CH2:16][C@H:15]([NH:17][C:18]4[S:19][C:20]([C:23]([N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)=[O:25])=[CH:21][N:22]=4)[CH2:14]3)[C:5]2=[O:26])[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178524766HCID 178524766, compound

Product 1

HCID 178519836HCID 178519836, compoundYield 30.1%

Procedure

The title compound was prepared following the procedure for EXAMPLE 151, using a mixture of 2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxylic acid, EXAMPLE 149, (0.07 g, 0.188 mmol), morpholine (0.025 ml, 0.282 mmol), diisopropylethylamine (0.049 ml, 0.282 mmol), and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (0.125 g, 0.282 mmol) to give 1-cyclopropyl-3-(trans-3-((5-(morpholine-4-carbonyl)thiazol-2-yl)amino)cyclobutyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.025 g, 0.057 mmol, 30.1% yield). m/z: 442.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ: ppm 8.30 (d, J=5.67 Hz, 1 H), 7.81-8.10 (m, 2 H), 7.13 (s, 1 H), 5.13 (t, J=8.31 Hz, 1 H), 4.32 (d, J=4.50 Hz, 1 H), 3.77 (br. s., 2 H), 3.58 (br. s., 6 H), 3.12-3.27 (m, 2 H), 2.85-3.03 (m, 1 H), 2.28-2.46 (m, 2 H), 0.89-1.10 (m, 4 H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a2b8753eea4646d0b8ec4090dc63e7c3
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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