2-Chloro-5-propylpyrimidine → 6-Bromo-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)thiazolo[4,5-b]pyridine

HRID 1429539Notes

Reaction equation

HRID 1429539 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[S:10][C:9]([O:11][CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[N:8][C:5]2=[N:6][CH:7]=1.Cl[C:19]1[N:24]=[CH:23][C:22]([CH2:25][CH2:26][CH3:27])=[CH:21][N:20]=1.BrC1C=CC2N=C(OC3CCN(C4N=CC(CCC)=CN=4)CC3)SC=2C=1>>[Br:1][C:2]1[CH:3]=[C:4]2[S:10][C:9]([O:11][CH:12]3[CH2:17][CH2:16][N:15]([C:19]4[N:24]=[CH:23][C:22]([CH2:25][CH2:26][CH3:27])=[CH:21][N:20]=4)[CH2:14][CH2:13]3)=[N:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 27357842-Chloro-5-propylpyrimidineHCID 674627896-Bromo-2-(piperidin-4-yloxy)thiazolo[4,5-b]pyridineHCID 674627936-Bromo-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole

Product 1

HCID 674669036-Bromo-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)thiazolo[4,5-b]pyridine

Procedure

Compound 21D was prepared from Compound 21C and 2-chloro-5-propylpyrimidine in a similar manner to the procedure described for Compound 1C in Example 1. 1H NMR (400 MHz, chloroform-d) δ ppm 8.55 (d, J=2.2 Hz, 1H), 8.16 (s, 2H), 8.08 (d, J=2.2 Hz, 1H), 5.58 (dt, J=8.2, 4.1 Hz, 1H), 4.20-4.34 (m, 2H), 3.52-3.65 (m, 2H), 2.40 (t, J=7.7 Hz, 2H), 2.16-2.28 (m, 2H), 1.84-2.01 (m, J=12.9, 8.7, 8.7, 3.8 Hz, 2H), 1.49-1.64 (m, J=7.5, 7.5, 7.5, 7.3, 7.1 Hz, 2H), 0.93 (t, J=7.1 Hz, 3H). LC/MS (m/z)=435 (M+H)+.

Sources & evidence

ORD record
ord-7ae1c2924cc24f67a5c0d5ab2c60dc84
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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