2-(1-(5-Propylpyrimidin-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole → 6-(Piperazin-1-yl)-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole

HRID 1429530Notes

Reaction equation

HRID 1429530 reaction equation
[CH2:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[S:18][C:19]4[CH:25]=[C:24]([N:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)[CH:23]=[CH:22][C:20]=4[N:21]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)[CH2:2][CH3:3].C(C1C=NC(N2CCC(OC3SC4C=C(C5CCNCC=5)C=CC=4N=3)CC2)=NC=1)CC>>[N:26]1([C:24]2[CH:23]=[CH:22][C:20]3[N:21]=[C:17]([O:16][CH:13]4[CH2:12][CH2:11][N:10]([C:7]5[N:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][N:6]=5)[CH2:15][CH2:14]4)[S:18][C:19]=3[CH:25]=2)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 674627952-(1-(5-Propylpyrimidin-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazoleHCID 68208554tert-Butyl 4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)piperazine-1-carboxylate

Product 1

HCID 674627486-(Piperazin-1-yl)-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole

Procedure

Compound 12B was synthesized from Compound 12A in a similar manner to the procedure described for Compound 1E. 1H NMR (500 MHz, chloroform-d) δ ppm 8.17 (2H, s), 7.57 (1H, d, J=8.8 Hz), 7.18 (1H, d, J=2.5 Hz), 7.02 (1H, dd, J=8.8, 2.5 Hz), 5.36-5.44 (1H, m), 4.21 (2H, ddd, J=13.3, 6.8, 3.9 Hz), 3.62-3.73 (2H, m), 3.15-3.25 (4H, m), 3.05-3.15 (4H, m), 2.41 (2H, t, J=7.6 Hz), 2.11-2.23 (2H, m), 1.93 (2H, dddd, J=12.7, 8.4, 8.2, 4.0 Hz), 1.53-1.64 (2H, m), 0.92-0.98 (3H, m). LC/MS (m/z)=439 (M+H)+.

Sources & evidence

ORD record
ord-0d9ffadb41e342b390f4c7be683f022e
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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