tert-butyl [(1S,2R)-2-({6-carbamoyl-5-[(5-hydroxy-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)cyclohexyl]carbamate → HCID 178429073, compound

HRID 1504758Notes

Reaction equation

HRID 1504758 reaction equation
ClC1C=C(C)N=C(NC2C=C(N[C@@H]3CCCC[C@@H]3NC(=O)[O:27]C(C)(C)C)C=NC=2C#N)C=1.[C:33]([C:36]1[N:41]=[CH:40][C:39]([NH:42][C@@H:43]2[CH2:48][CH2:47][CH2:46][CH2:45][C@@H:44]2[NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[CH:38][C:37]=1[NH:57][C:58]1[CH:63]=[CH:62][C:61](O)=[C:60]([CH3:65])[N:59]=1)(=[O:35])[NH2:34]>>[C:33]([C:36]1[N:41]=[CH:40][C:39]([NH:42][C@@H:43]2[CH2:48][CH2:47][CH2:46][CH2:45][C@@H:44]2[NH:49][C:50](=[O:56])[O:51][C:52]([CH3:54])([CH3:53])[CH3:55])=[CH:38][C:37]=1[NH:57][C:58]1[CH:63]=[C:62]([OH:27])[CH:61]=[C:60]([CH3:65])[N:59]=1)(=[O:35])[NH2:34]

Participants

3

Reactant 2

HCID 86731654tert-butyl [(1S,2R)-2-({6-carbamoyl-5-[(5-hydroxy-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)cyclohexyl]carbamateHCID 86731656tert-butyl (1S,2R)-2-(5-(4-chloro-6-methylpyridin-2-ylamino)-6-cyanopyridin-3-ylamino)cyclohexylcarbamate

Product 1

HCID 178429073HCID 178429073, compound

Procedure

This example describes the conversion of (D13) to (E15) as shown in Scheme 3. tert-butyl [(1S,2R)-2-({6-carbamoyl-5-[(4-hydroxy-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)cyclohexyl]carbamate was prepared from tert-butyl [(1S,2R)-2-({5-[(4-chloro-6-methylpyridin-2-yl)amino]-6-cyanopyridin-3-yl}amino)cyclohexyl]carbamate (PrepEx 1.7) using chemistry analogous to that described for the synthesis of tert-butyl [(1S,2R)-2-({6-carbamoyl-5-[(5-hydroxy-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)cyclohexyl]carbamate (PrepEx 1.9). MS ESI calc'd. for C23H33N6O4 [M+H]+ 457. found 457.

Sources & evidence

ORD record
ord-9f3d2e4f5fe84af59d05c067913e42f7
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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