Di-tert-butyl {5-[(tert-butoxycarbonyl)amino]-3-chloropyridin-2-yl}imidodicarbonate → N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-3-chloropyridine-2,5-diamine

HRID 1039078Notes

Reaction equation

HRID 1039078 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=3)[CH2:19][CH2:18]2)(=O)=O)=CC=1.C(OC([NH:37][C:38]1[CH:39]=[C:40]([Cl:59])[C:41]([N:44](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[N:42][CH:43]=1)=O)(C)(C)C>>[Cl:29][C:26]1[CH:27]=[N:28][C:23]([N:20]2[CH2:19][CH2:18][CH:17]([C@H:15]3[CH2:16][C@H:14]3[CH2:13][CH2:12][NH:44][C:41]3[C:40]([Cl:59])=[CH:39][C:38]([NH2:37])=[CH:43][N:42]=3)[CH2:22][CH2:21]2)=[N:24][CH:25]=1

Participants

3

Reactant 2

HCID 67962202Di-tert-butyl {5-[(tert-butoxycarbonyl)amino]-3-chloropyridin-2-yl}imidodicarbonateHCID 866661412-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate

Product 1

HCID 67778696N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-3-chloropyridine-2,5-diamine

Procedure

The title compound was synthesized by procedure analogous to Step 2 of Example 11 from cis-2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate from Step 1 of Example 5 and di-tert-butyl {5-[(tert-butoxycarbonyl)amino]-3-chloropyridin-2-yl}imidodicarbonate from Step 1 of this example.

Sources & evidence

ORD record
ord-f3ef63885d1448eebeace699edd3cfe1
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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