Triethylamine → HCID 54684191, compound

HRID 1012996Notes

Reaction equation

HRID 1012996 reaction equation
[CH3:1][N:2]([C:4](=[O:27])[C:5]([N:7]([CH3:26])[CH:8]1[CH2:14][N:13]([CH3:15])[CH2:12][CH2:11][N:10]2[C:16](=[O:25])[C:17]([OH:24])=[C:18]([C:20]([O:22]C)=O)[N:19]=[C:9]12)=[O:6])[CH3:3].C(N(CC)CC)C.[F:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][CH:37]=1>CO>[F:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH:41][C:20]([C:18]2[N:19]=[C:9]3[CH:8]([N:7]([CH3:26])[C:5](=[O:6])[C:4]([N:2]([CH3:3])[CH3:1])=[O:27])[CH2:14][N:13]([CH3:15])[CH2:12][CH2:11][N:10]3[C:16](=[O:25])[C:17]=2[OH:24])=[O:22])=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 67317152HCID 67317152, compound

Product 1

HCID 54684191HCID 54684191, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 10-[[(dimethylamino)(oxo)acetyl](methyl)amino]-3-hydroxy-8-methyl-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-d][1,4]diazepine-2-carboxylate prepared as described in Step 2 was dissolved in methanol and treated with 1.2 eq. of triethylamine and 1.2 eq. of 4-fluorobenzylamine. The reaction mixture was refluxed overnight, then cooled to room temperature and purified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant) affording desired compound (trifluoroacetic salt) as a white solid. 1H NMR (300 MHz, CD3CN) δ 12.4 (bs, 1H), 10.01 (bs, 1H), 7.63 (dd, J=8.6 Hz, J=5.7 Hz, 2H), 7.29 (t, J=8.6 Hz, 2H), 5.53-5.30 (m, 2H), 4.82-4.68 (m, 2H), 4.25-4.13 (m, 3H), 3.95 (bs, 1H), 3.48-3.42 (m, 1H), 3.25 (s, 3H), 3.20 (s, 3H), 3.19 (s, 3H), 3.13 (s, 3H); MS (ES) C22H27FN6O5 requires 474. Found: 475 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. custompurified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant)

Sources & evidence

ORD record
ord-25c84d9346d54d7aaa71c1b6407f1f3a
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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