Triphosgene → (1S,4S)-2-Oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic acid [2-((R)-indan-1-ylamino)-quinolin-6-yl]-amide

HRID 1928734Notes

Reaction equation

HRID 1928734 reaction equation
[C:1](=[O:12])(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[C@H:13]12[CH2:19][C@H:16]([NH:17][CH2:18]1)[CH2:15][O:14]2.[C@H:20]1([NH:29][C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([NH2:40])[CH:36]=3)[N:31]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1>>[C@H:20]1([NH:29][C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([NH:40][C:1]([N:17]4[CH2:18][C@@H:13]5[CH2:19][C@H:16]4[CH2:15][O:14]5)=[O:12])[CH:36]=3)[N:31]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 11159293(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrobromideHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Product 1

HCID 86634162(1S,4S)-2-Oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic acid [2-((R)-indan-1-ylamino)-quinolin-6-yl]-amide

Procedure

The title compound was prepared in accordance with the general method 4 described in example 16 from bis(trichloromethyl) carbonate, (1S,4S)-2-oxa-5-aza-bicyclo[2.2.1]heptane and (R)—N2-indan-1-yl-quinoline-2,6-diamine; MS: m/e=401.6 (M+H+).

Sources & evidence

ORD record
ord-d5ea96ebc67f4f54a6d0d7c781646c6e
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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