Trifluoroacetic acid methylene chloride → HCID 54684174, compound

HRID 1012993Notes

Reaction equation

HRID 1012993 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][C:40]=1[CH3:41])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]2[CH:17]([N:18]([C:20](=[O:26])[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH3:19])[CH2:16][N:15]([C:27](OC(C)(C)C)=O)[CH2:14][CH2:13][N:12]2[C:34](=[O:37])[C:35]=1[OH:36])=[O:8].ClCCl.F[C:46](F)(F)[C:47](O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][C:40]=1[CH3:41])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]2[CH:17]([N:18]([CH3:19])[C:20](=[O:26])[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH2:16][N:15]([CH:27]3[CH2:47][CH2:46]3)[CH2:14][CH2:13][N:12]2[C:34](=[O:37])[C:35]=1[OH:36])=[O:8]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 67317141HCID 67317141, compound

Product 1

HCID 54684174HCID 54684174, compound

Procedure

The compound of Step 2 was stirred in dichloromethane/trifluoroacetic acid (8/2 v/v) for 1 hour, then concentrated under reduced pressure and triturated with diethyl ether. A portion of this material was purified by prep RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant) affording title compound as a white solid. 1H NMR (400 MHz, CD3CN) δ 12.40 (bs, 1H), 9.78 (bs, 1H), 7.43 (s, 1H), 7.28-7.21 (m, 2H), 5.37-5.29 (m, 2H), 4.58 (dd, J=14.6 Hz, J=6.86 Hz, 1H), 4.47 (dd, J=14.6 Hz, J=6.41 Hz, 1H), 4.01-3.3.92 (m, 3H), 3.78-3.69 (m, 1H), 3.22-3.12 (m, 1H), 3.08 (s, 3H), 2.93 (s, 3H), 2.91 (s, 3H), 2.28 (s, 3H); MS (ES) C22H27ClN6O5 requires 490. Found: 491 (M+H+). N-(2-{[(3-chloro-4-methylbenzyl)amino]carbonyl}-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-d][1,4]diazepin-10-yl)-N,N′,N′-trimethylethanediamide has been resolved into its enantiomers by semipreparative chiral SFC using the following conditions:

Workup

  1. concentrationconcentrated under reduced pressure
  2. customtriturated with diethyl ether
  3. customA portion of this material was purified by prep RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant)

Sources & evidence

ORD record
ord-df99545c6d76403d98478a39b25582c4
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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