Triphosgene → 1-[2-(8-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylamino)-quinolin-6-yl]-3-((s)-1-methyl-pyrrolidin-3-yl)-urea

HRID 1928761Notes

Reaction equation

HRID 1928761 reaction equation
[C:1](=O)(OC(Cl)(Cl)Cl)[O:2]C(Cl)(Cl)Cl.[CH3:13][N:14]1[CH2:18][CH2:17][C@H:16]([NH2:19])[CH2:15]1.[CH3:20][O:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[CH:30]([NH:32][C:33]1[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[C:38]([NH2:43])[CH:39]=3)[N:34]=1)[CH2:29][CH2:28][CH2:27]2>>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[CH:30]([NH:32][C:33]1[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[C:38]([NH:43][C:1]([NH:19][C@H:16]4[CH2:17][CH2:18][N:14]([CH3:13])[CH2:15]4)=[O:2])[CH:39]=3)[N:34]=1)[CH2:29][CH2:28][CH2:27]2

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 21307223(3S)-1-methylpyrrolidin-3-amineHCID 57860959Rac-n2-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-quinoline-2,6-diamine

Product 1

HCID 442187201-[2-(8-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylamino)-quinolin-6-yl]-3-((s)-1-methyl-pyrrolidin-3-yl)-urea

Procedure

The title compound was prepared in accordance with the general method 4 described in example 16 from bis(trichloromethyl) carbonate, (3S)-1-methyl-3-pyrrolidinamine (CAS no. 214357-95-6) and rac-N2-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-quinoline-2,6-diamine; MS: m/e=446.2 (M+H+).

Sources & evidence

ORD record
ord-3cd061e0b6334d219cec9b064f59ad4a
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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