Phenyl isocyanate → HCID 67005746, compound

HRID 562801Notes

Reaction equation

HRID 562801 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)[CH:24]=4)[N:17]=2)[CH:13]=[CH:12][S:11]3)[CH:5]=[CH:6][CH:7]=1.NC1C=C(C2N=C3N(C=2C2C=CN=C(NC4C=CC=C(OCCCN5CCOCC5)C=4)N=2)C=CS3)C=CC=1.[N:75]([C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)=[C:76]=[O:77].FC1C=CC=C(F)C=1C(Cl)=O>>[N:31]1([CH2:30][CH2:29][C:25]2[CH:24]=[C:23]([NH:22][C:18]3[N:17]=[C:16]([C:15]4[N:14]5[C:10]([S:11][CH:12]=[CH:13]5)=[N:9][C:8]=4[C:4]4[CH:3]=[C:2]([NH:1][C:76]([NH:75][C:78]5[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=5)=[O:77])[CH:7]=[CH:6][CH:5]=4)[CH:21]=[CH:20][N:19]=3)[CH:28]=[CH:27][CH:26]=2)[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1

Participants

5

Reactant 4

HCID 7672Phenyl isocyanateHCID 874382,6-Difluorobenzoyl chlorideHCID 67005647HCID 67005647, compoundHCID 67006333HCID 67006333, compound

Product 1

HCID 67005746HCID 67005746, compound

Procedure

The title compound was prepared as described in EXAMPLE 297, with the following substitutions: 4-(6-(3-aminophenyl)imidazo[2,1-b]thiazol-5-yl)-N-(3-(2-morpholinoethyl)phenyl)pyrimidin-2-amine for 4-(6-(3-aminophenyl)imidazo[2,1-b]thiazol-5-yl)-N-(3-(3-morpholinopropoxy)phenyl)pyrimidin-2-amine and isocyanatobenzene for 2,6-difluorobenzoyl chloride. (ESI(+)) m/e 617 (M+H)+; (ESI(−)) m/e 615 (M−H)−; 1H-NMR (300 MHz, DMSO-d6) □9.65 (s, 1H), 8.84 (s, 2H), 8.70 (s, 1H), 8.29 (d, 1H), 7.74 (t, 1H), 7.49-7.63 (m, 4H), 7.43-7.48 (m, 2H), 7.39 (t, 1H), 7.16-7.31 (m, 4H), 6.92-7.01 (m, 1H), 6.87 (d, 1H), 6.63 (d, 1H), 3.52-3.60 (m, 4H), 2.66-2.77 (m, 2H), 2.52-2.57 (m, 2H), 2.36-2.44 (m, 4H).

Sources & evidence

ORD record
ord-a00e77d202bb4f9f8b7f84bd1f050293
Source dataset
uspto-grants-2011_11
Patent number
US08067409B2

Reaction notes

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