Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → tert-Butyl 4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)thiazolo[4,5-b]pyridin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1429540Notes

Reaction equation

HRID 1429540 reaction equation
Br[C:2]1[CH:3]=[C:4]2[S:10][C:9]([O:11][CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[N:23]=[CH:22][C:21]([CH2:24][CH2:25][CH3:26])=[CH:20][N:19]=4)[CH2:14][CH2:13]3)=[N:8][C:5]2=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH:36]=2)O1.C(C1C=NC(N2CCC(OC3SC4C=C(C5CCN(C(OC(C)(C)C)=O)CC=5)C=CC=4N=3)CC2)=NC=1)CC>>[CH2:24]([C:21]1[CH:20]=[N:19][C:18]([N:15]2[CH2:16][CH2:17][CH:12]([O:11][C:9]3[S:10][C:4]4[C:5]([N:8]=3)=[N:6][CH:7]=[C:2]([C:35]3[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH:36]=3)[CH:3]=4)[CH2:13][CH2:14]2)=[N:23][CH:22]=1)[CH2:25][CH3:26]

Participants

4

Reactant 3

HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 67464591tert-Butyl 4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylateHCID 674669036-Bromo-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)thiazolo[4,5-b]pyridine

Product 1

HCID 71275299tert-Butyl 4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)thiazolo[4,5-b]pyridin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

Compound 21E was prepared from Compound 21D and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate in a similar manner to the procedure described for Compound 1D in Example 1. 1H NMR (400 MHz, chloroform-d) δ ppm 8.55 (d, J=2.2 Hz, 1H), 8.17 (s, 2H), 7.93 (d, J=2.2 Hz, 1H), 6.10 (br. s., 1H), 5.52-5.66 (m, 1H), 4.21-4.33 (m, 2H), 4.12 (br. s., 2H), 3.68 (t, J=5.5 Hz, 2H), 3.50-3.64 (m, 2H), 2.56 (br. s., 2H), 2.41 (t, J=7.4 Hz, 2H), 2.24 (ddd, J=9.8, 6.2, 3.3 Hz, 2H), 1.94 (dddd, J=12.8, 8.8, 8.7, 3.8 Hz, 2H), 1.53-1.71 (m, 3H), 1.45-1.54 (m, 9H), 0.94 (t, J=7.4 Hz, 3H). LC/MS (m/z)=537 (M+H)+.

Sources & evidence

ORD record
ord-c495e2a13423434cb07d64d2553d6df4
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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