(2-Methoxyethyl)(methyl)amine → N-(7-[1,4]Dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-2-pyrrolidin-1-ylmethyl-isonicotinamide

HRID 2222172Notes

Reaction equation

HRID 2222172 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][N:29]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[C:17]([CH:18]3[CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19]3)=[CH:16][CH:15]=[C:14]([O:25][CH3:26])[C:12]=2[N:13]=1)=[O:7].COCCNC.COCCN(CC1C=C(C=CN=1)C(NC1S[C:51]2[C:57]([N:58]3[CH2:63][CH2:62]OCC3)=CC=C(OC)C=2N=1)=O)C>>[O:23]1[CH2:24][CH:18]([C:17]2[C:11]3[S:10][C:9]([NH:8][C:6](=[O:7])[C:5]4[CH:27]=[CH:28][N:29]=[C:3]([CH2:2][N:58]5[CH2:57][CH2:51][CH2:62][CH2:63]5)[CH:4]=4)=[N:13][C:12]=3[C:14]([O:25][CH3:26])=[CH:15][CH:16]=2)[CH2:19][O:20][CH2:21][CH2:22]1

Participants

4

Reactant 3

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 229934162-{[(2-Methoxy-ethyl)-methyl-amino]-methyl}-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamideHCID 865951462-Chloromethyl-N-(7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 86595150N-(7-[1,4]Dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-2-pyrrolidin-1-ylmethyl-isonicotinamideYield 48%

Procedure

2-Chloromethyl-N-(7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide and N-(2-methoxyethyl)-methylamine were reacted as described for 2-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide in WO03/043636. Usual workup, preparative reversed-phase HPLC and final dry-freezing afforded the tide compound as light yellow solid (48% yield). Mp 108-111° C., MS: m/e=469(M+H+).

Workup

  1. customUsual workup, preparative reversed-phase HPLC and final dry-freezing

Sources & evidence

ORD record
ord-dd83651cf02b4b43b4b46d688eadf00b
Source dataset
uspto-grants-2008_05
Patent number
US07371748B2

Reaction notes

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