Thionyl Chloride → N-(2-(3-(Chloromethyl)-6-(cyclopropylmethoxy)quinolin-2-ylamino)ethyl)acetamide hydrochloride

HRID 1620307Notes

Reaction equation

HRID 1620307 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])[C:10]([CH2:23]O)=[CH:9]3)[CH2:3][CH2:2]1.O=S(Cl)[Cl:27]>C(Cl)Cl>[ClH:27].[Cl:27][CH2:23][C:10]1[C:11]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])=[N:12][C:13]2[C:8]([CH:9]=1)=[CH:7][C:6]([O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)=[CH:15][CH:14]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182276N-(2-(6-(Cyclopropylmethoxy)-3-(hydroxymethyl)quinolin-2-ylamino)ethyl)acetamide2×

Product 1

HCID 68182271N-(2-(3-(Chloromethyl)-6-(cyclopropylmethoxy)quinolin-2-ylamino)ethyl)acetamide hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(2-(6-(cyclopropylmethoxy)-3-(hydroxymethyl)quinolin-2-ylamino)ethyl)acetamide SLA 47096A (0.374 g, 1.1 mmol) in dry CH2Cl2 (11 mL) in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (1.65 mL, 22.7 mmol). The mixture was stirred for 2 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give N-(2-(3-(chloromethyl)-6-(cyclopropylmethoxy)quinolin-2-ylamino)ethyl)acetamide hydrochloride SLA 47096B as a yellow solid (0.475 g, 100% yield).

Workup

  1. concentrationthen concentrated to dryness at 40° C. under vacuum
  2. concentrationThe residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times)

Sources & evidence

ORD record
ord-91a570416011487da40ee982c5b3c617
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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