Methanol → HCID 23598691, compound

HRID 891205Notes

Reaction equation

HRID 891205 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][N:5]1[CH2:11][C:10]([CH2:12][NH2:13])=[CH:9][CH2:8][CH:7]([NH:14][C:15]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][N:18]=2)=[O:16])[C:6]1=[O:27].[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C.CO>C1COCC1>[CH3:1][O:2][C:3](=[O:28])[CH2:4][N:5]1[CH2:11][C:10]([CH2:12][NH:13][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:9][CH2:8][CH:7]([NH:14][C:15]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][N:18]=2)=[O:16])[C:6]1=[O:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 23598689HCID 23598689, compound

Product 1

HCID 23598691HCID 23598691, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {6-(aminomethyl)-3-[(isoquinoline-1-carbonyl)-amino]-2-oxo-2,3,4,7-tetrahydro-azepin-1-yl}-acetic acid methyl ester, 29, (0.14 g, 0.37 mmol) in THF(1 mL) is added benzoyl chloride (80 μl, 0.75 mmol) and triethyl amine (0.71 mL, 4.99 mmol). The reaction is complete with a few minutes. Methanol (5 mL) is added to the reaction mixture and then the solvents are removed in vacuo to provide a residue which is purified by HPLC to afford 84 mg (46% yield) of the desired product. 1H NMR (CDCl3) δ 9.37–9.33 (d, J=9.4 Hz, 1H), 9.06–9.03 (d, J=5.5 Hz, 1H), 7.73–7.64 (m, 4H), 7.59–7.48 (m, 2H), 7.41–7.48 (m, 4H), 5.68 (bs, 1H), 5.37–5.30 (m, 1H), 4.644.57 (d, d, J=17.5, 2.37 Hz, 1H), 4.4.6–4.40 (d, J=17.6 Hz, 1H), 4.15–4.08 (d, d, J=14.5, 6.9 Hz, 1H), 3.82–3.76 (d, J=17.6 Hz, 1H), 3.76–3.70 (d, d, J=14.7 Hz, 1H), 3.42 (s, 3H), 3.38–3.33 (d, J=17.6 Hz, 1H), 2.81–2.76 (m, 1H), 2.35–2.25 (d, d, J=16.3, 14.2 Hz, 1H); 13C (CDCl3) 172.6, 170.5, 168.0, 165.9, 148.2, 141.0, 137.7, 134.3, 133.8, 132.4, 132.3, 132.0, 130.7, 129.0, 128.9, 127.7, 127.6, 127.5, 127.2, 124.7, 52.6, 50.5, 49.3, 49.1, 46.7, 32.6; MS 487 (M+H).

Workup

  1. waitThe reaction is complete with a few minutes
  2. customthe solvents are removed in vacuo
  3. customto provide a residue which
  4. customis purified by HPLC

Sources & evidence

ORD record
ord-68049314e5ad461d85c68fde0a77873d
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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