1-Pyrrolidineethanamine → 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)-N-(2-(pyrrolidin-1-yl)ethyl)benzamide hydrochloride

HRID 910998Notes

Reaction equation

HRID 910998 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]2[S:21][CH:22]=[C:23]([CH3:25])[N:24]=2)[CH:14]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:39][CH2:40][CH2:41][N:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1>CN(C=O)C>[ClH:2].[Cl:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:39][CH2:40][CH2:41][N:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:9])=[CH:5][C:4]=1[O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]2[S:21][CH:22]=[C:23]([CH3:25])[N:24]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 248266634-Chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid hydrochloride

Product 1

HCID 866347384-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)-N-(2-(pyrrolidin-1-yl)ethyl)benzamide hydrochlorideYield 33.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following procedure of Example 83, 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid hydrochloride (0.1 g, 0.2511 mmol), triethylamine (0.1016 g, 1.004 mmol), DMF (3 mL), added ethyl carbonochloridate (0.02641 mL, 0.2762 mmol), N-(2-aminoethyl)pyrrolidine (0.05734 g, 0.5022 mmol) were reacted to afford 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)-N-(2-(pyrrolidin-1-yl)ethyl)benzamide hydrochloride (0.021 g, 15.22% yield) as off white solid. 1H NMR (DMSO) δ 11.26 (bs, 1H), 10.18 (bs, 1H), 8.98 (t, 1H), 8.23 (d, 1H), 7.92 (dd, 1H), 7.89 (d, 1H), 7.83 (d, 1H), 6.58 (m, 3H), 3.61 (m, 4H), 3.31 (q, 2H), 3.02 (m, 2H), 2.21 (d, 3H), 2.00 (m, 2H), 1.86 (m, 2H); Mass spectrum (esi) m/z 458 (100) (M+H—HCl).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2a65089bc5a0458b81681502ebeda3ae
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…