2-Methoxyethyl chloroformate → 2-Methoxyethyl 4-(6-(1-(propylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazol-2-yloxy)piperidine-1-carboxylate

HRID 1429543Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[S:9][C:10]3[CH:16]=[C:15]([C:17]4[CH2:18][CH2:19][N:20]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[CH2:21][CH:22]=4)[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:3][CH2:2]1.[C:29](Cl)(=[O:35])[O:30][CH2:31][CH2:32][O:33][CH3:34]>>[CH2:26]([S:23]([N:20]1[CH2:19][CH:18]=[C:17]([C:15]2[CH:14]=[CH:13][C:11]3[N:12]=[C:8]([O:7][CH:4]4[CH2:3][CH2:2][N:1]([C:29]([O:30][CH2:31][CH2:32][O:33][CH3:34])=[O:35])[CH2:6][CH2:5]4)[S:9][C:10]=3[CH:16]=2)[CH2:22][CH2:21]1)(=[O:25])=[O:24])[CH2:27][CH3:28]

Participants

Reactant 2

HCID 694002-Methoxyethyl chloroformate

HCID 67468519HCID 67468519, compound

Product 1

HCID 545965282-Methoxyethyl 4-(6-(1-(propylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazol-2-yloxy)piperidine-1-carboxylate

Procedure

Example 25 was prepared from Compound 15A and 2-methoxyethyl carbonochloridate in a similar manner to the procedure described in Example 15. 1H NMR (599 MHz, DMSO-d6) δ ppm 8.22 (s, 1H), 7.88 (s, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.46 (d, J=8.8 Hz, 1H), 6.19 (br. s., 1H), 5.28-5.39 (m, 2H), 4.05-4.19 (m, 2H), 3.92 (br. s., 2H), 3.65-3.77 (m, 2H), 3.49-3.58 (m, 2H), 3.45 (t, J=5.6 Hz, 2H), 2.96-3.11 (m, 2H), 2.60 (br. s., 2H), 2.08 (d, J=8.8 Hz, 3H), 1.63-1.84 (m, 6H), 1.00 (t, J=7.3 Hz, 3H). LC/MS (m/z)=524 (M+H)+.

Sources & evidence

ORD record: ord-0b42dc30948f4e4a9246f28e8befa631
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940716B2

Reaction notes

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