Benzylamine → HCID 23598690, compound

HRID 891200Notes

Reaction equation

HRID 891200 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][N:5]1[CH2:11][C:10]([CH2:12]S(C)(=O)=O)=[CH:9][CH2:8][CH:7]([NH:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][N:21]=2)=[O:19])[C:6]1=[O:30].[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.FC(F)(F)C([O-])=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:31])[CH2:4][N:5]1[CH2:11][C:10]([CH2:12][NH:39][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:9][CH2:8][CH:7]([NH:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][N:21]=2)=[O:19])[C:6]1=[O:30]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 84468TrifluoroacetateHCID 69601283HCID 69601283, compound

Product 1

HCID 23598690HCID 23598690, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the crude product from the previous reaction, {6-[(methanesulfonyl)methyl]-3-[(isoquinoline-1-carbonyl)-amino]-2-oxo-2,3,4,7-tetrahydro-azepin-1-yl}-acetic acid methyl ester, 23, (0.147 g, 0.32 mmol) in CH2Cl2 (1 mL), is added benzylamine (1 mL). The reaction is stirred at room temperature for 10 minutes, then the reaction is diluted with CH2Cl2. The organic layer is washed with saturated NaHCO3, saturated NaCl, and dried (Na2SO4). The solvent is removed in vacuo and the resulting crude material is purified by HPLC to afford 82 mg (44% yield) of the desired product as the trifluoroacetate salt. 1H (CDCl3) δ 8.82–8.79 (d, J=6.1 Hz, 1H), 8.61–8.59 (d, J=8.6 Hz, 1H), 8.33–8.31, (d, J=5.8 Hz, 1H), 8.01–7.99 (d, J=5.94 Hz, 1H), 7.95–7.82 (m, 2H), 7.77–7.72 (d, d, J=7.98, 7.98 Hz, 1H), 7.36–7.18 (m, 5H), 5.91 (bs, 1H), 5.40–5.39 (m, 1H), 4.67–4.61 (d, J=17.4 Hz, 1H), 4.55–4.49 (d, J=17.8 Hz, 1H), 4.19–4.05 (m, 1H), 3.88–3.83 (d, J=14.7 Hz, 1H), 3.77–3.57 (m, 3H), 3.50 (s, 3H), 2.84–2.78 (d, J=17.8 Hz, 1H), 2.50–2.40 (d, d, J=15.8, 14.5 Hz, 1H); 13C (CDCl3) 171.9, 171.5, 161.9, 161.4, 160.9, 160.6, 149.1, 139.1, 135.2, 134.7, 134.2, 131.3, 130.3, 130.2, 130.1, 129.6, 128.2, 127.9, 127.8, 127.4, 125.8, 121.5, 117.7, 113.8, 110.0, 53.5, 52.9, 51.6, 49.8, 48.3, 37.9, 31.6; MS 473 (M+H)+.

Workup

  1. washThe organic layer is washed with saturated NaHCO3, saturated NaCl
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is removed in vacuo
  4. customthe resulting crude material is purified by HPLC

Sources & evidence

ORD record
ord-89a8e40138e94bf2ab924a2e53d98302
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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