HCID 9933379, compound → HCID 10224773, compound

HRID 133013Notes

Reaction equation

HRID 133013 reaction equation
[CH:1]1([CH2:4][C@H:5]([C@@H:28](O)[CH2:29][CH2:30][CH2:31][CH3:32])[C:6]([NH:8][CH:9]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=3[N:11]([CH3:26])[C:10]2=[O:27])=[O:7])[CH2:3][CH2:2]1.NC1N=C(C2C=CC=CN=2)C2C=CC=CC=2N(C)C1=O>>[O:7]=[C:6]([NH:8][CH:9]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=2[N:11]([CH3:26])[C:10]1=[O:27])[C@H:5]([CH2:4][CH:1]1[CH2:2][CH2:3]1)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

3

Reactant 2

HCID 9933379HCID 9933379, compoundHCID 9993071HCID 9993071, compound

Product 1

HCID 10224773HCID 10224773, compound

Procedure

(±)-3-(2-(R)-Cyclopropylmethyl-3-(S)-hydroxyl-1-oxoheptyl)amino-1-methyl-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one was made from 1 and 3-amino-1-methyl-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepine-2-one (G. Semple et al Synth. Commun. 1996, 26, 721) according to step 1 in Example 1. MS (ESI): 449 (M+H), 471 (M+Na), 447 (M−H). This diastereomeric mixture was submitted to chiral separation on a Chiralpak AD column with 10-15% i-propanol/hexane. The 2nd eluting peak was converted to Example 10 by the same procedures of steps 2 and 3 in Example 1. MS (ESI): 433.3 (M+H).

Workup

  1. customThis diastereomeric mixture was submitted to chiral separation on a Chiralpak AD column with 10-15% i-propanol/hexane
  2. washThe 2nd eluting peak

Sources & evidence

ORD record
ord-fe43edf3f8484d52a7542e748386303d
Source dataset
uspto-grants-2008_06
Patent number
US07390802B2

Reaction notes

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