4-(2-Chloroethyl)morpholine → HCID 10458706, compound

HRID 2113966Notes

Reaction equation

HRID 2113966 reaction equation
Br[CH2:2][CH2:3][C:4]([NH:6][C:7]1[S:8][C:9]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:14]=2)=[C:10]([CH3:12])[N:11]=1)=[O:5].[N:27]1([CH2:33][CH2:34][NH2:35])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.NCCC(NC1SC(C2C=CN=C(NC3C=CC(Cl)=CC=3)N=2)=C(C)N=1)=O.ClCCN1CCOCC1>CC#N>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:15]2[N:14]=[C:13]([C:9]3[S:8][C:7]([NH:6][C:4](=[O:5])[CH2:3][CH2:2][NH:35][CH2:34][CH2:33][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[N:11][C:10]=3[CH3:12])[CH:18]=[CH:17][N:16]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 767274-(2-Chloroethyl)morpholineHCID 4082852-MorpholinoethylamineHCID 86600462HCID 86600462, compoundHCID 86600463HCID 86600463, compound

Product 1

HCID 10458706HCID 10458706, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

By treatment of 3-bromo-N-{5-[2-(4-chloro-phenylamino)-pyrimidin-4-yl]-4-methyl-thiazol-2-yl}-propionamide with 2-morpholin-4-yl-ethylamine (or 3-amino-N-{5-[2-(4-chloro-phenylamino)-pyrimidin-4-yl]-4-methyl-thiazol-2-yl}-propionamide with 4-(2-chloro-ethyl)-morpholine. Anal. RP-HPLC: tR=11.5 min (10-70% MeCN, purity>97%). 1H-NMR (DMSO-D6) δ 1.52 (d, 2H, J=7.0 Hz, CH2), 2.48 (m, 2H, CH2), 2.52 (s, 3H, CH3), 3.05-3.11 (m, 4H, CH2), 3.25-3.28 (m, 6H, CH2), 4.08 (m, 2H, CH2), 7.13 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 7.29 (m, 2H, Ph-H), 7.82 (m, 2H, Ph-H), 8.51 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 9.82 (brs, 1H, NH).

Sources & evidence

ORD record
ord-2111bc05c2544e8fbb2f7986012c1c56
Source dataset
uspto-grants-2008_10
Patent number
US07432260B2

Reaction notes

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