4-(Isocyanatomethyl)oxane → 1-[3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-yl]-3-(tetrahydro-2H-pyran-4-ylmethyl)urea

HRID 1912905Notes

Reaction equation

HRID 1912905 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[C:2]=[O:3].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([NH2:27])=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[N:23][C:22]=23)=[CH:14][CH:13]=1>>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([NH:27][C:2]([NH:1][CH2:4][CH:5]3[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)=[O:3])=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[N:23][C:22]=23)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 242297484-(Isocyanatomethyl)oxaneHCID 687512953-(4-Chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 687517541-[3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-yl]-3-(tetrahydro-2H-pyran-4-ylmethyl)urea

Procedure

4-(Isocyanatomethyl)tetrahydropyran (Maybridge) and the product from Example 99A were processed using method analogous to that described in Example 99B to afford the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 8.51 (dd, J=6.9, 1.8 Hz, 1H), 8.47 (dd, J=4.1, 1.8 Hz, 1H), 8.21-8.31 (m, 1H), 7.54-7.56 (m, 2H), 7.46-7.49 (m, 2H), 6.89-6.90 (bs, 1H), 6.81 (dd, J=6.9, 4.1 Hz, 1H), 4.01 (dd, J=11.1, 3.6 Hz, 2H), 3.41 (td, J=11.7, 1.8 Hz, 2H), 3.33 (t, J=6.3 Hz, 2H), 1.84-1.95 (m, 1H), 1.69-1.75 (m, 2H), 1.42 (qd, J=12.3, 4.5 Hz, 2H); MS (ESI) m/z 386 (M+H)+; Anal. calculated for C19H20ClN5O2: C, 59.14; H, 5.22; N, 18.15; Cl, 9.19. Found C, 58.96; H, 5.13; N, 17.99; Cl, 9.39.

Sources & evidence

ORD record
ord-155da8dd875240a6bfaac627bc6800ff
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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