Ethyl acetimidate → HCID 136200149, compound

HRID 929117Notes

Reaction equation

HRID 929117 reaction equation
[CH3:1][C:2]1[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:3]=1[O:4][CH2:5][C@H:6]([OH:36])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[C:10]=1[C:16]1[NH:17][C:18]2[C:26]([N:27]=1)=[CH:25][C:24]1[C:23](=[O:28])[N:22]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[C:21](=[O:35])[C:20]=1[CH:19]=2.[C:42](=[NH:47])(OCC)[CH3:43]>CCN(CC)CC>[CH3:1][C:2]1[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:3]=1[O:4][CH2:5][C@H:6]([OH:36])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[C:10]=1[C:16]1[NH:17][C:18]2[C:26]([N:27]=1)=[CH:25][C:24]1[C:23](=[O:28])[N:22]([CH:29]3[CH2:30][CH2:31][N:32]([C:42](=[NH:47])[CH3:43])[CH2:33][CH2:34]3)[C:21](=[O:35])[C:20]=1[CH:19]=2

Participants

4

Reactant 2

HCID 65066Ethyl acetimidateHCID 136200147HCID 136200147, compound

Product 1

HCID 136200149HCID 136200149, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 2-{4-[(R)-3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-6-piperidin-4-yl-1H-1,3,6-triaza-s-indacene-5,7-dione (109 mg, 0.2 mmol) and ethyl acetimidate (3 g) in Et3N (8 mL) was stirred at the room temperature for 110 h. After it was concentrated at 35° C. (the bath temperature) under reduced pressure, the mixture was subjected to chromatography [CH2Cl2/MeOH/28% aqueous NH4OH (90:10:1)] to furnish a fluorescent product which was purified again with HPLC to afford the title compound in TFA salt form (5.06 mg, 3.6%). 1H NMR (DMSO-d6) δ 1.93 (m, 2H), 2.19 (s, 3H, CH3), 2.21 (s, 3H, CH3), 2.35 (s, 3H, CH3), 3.26 (m, 1H), 3.40 (m, 1H), 3.58 (m, 1H), 3.86 (m, 1H), 3.91-4.26 (7H), 4.43 (m, 1H), 6.23 (d, J=7 Hz, 1H), 6.86 (d, J=7 Hz, 1H), 6.92 (d, J=7 Hz, 1H), 7.00 (s, 1H), 7.41 (d, J=7 Hz, 1H), 7.71 (s, 1H), 8.10 (s, 1H), 8.68 (br s, 1H, NH), 9.21 (br s, 1H, NH), 10.97 (br s, 1H, NH), 11.30 (br s, 1H, NH); ESI-MS m/z 598.7 (MH+).

Workup

  1. concentrationAfter it was concentrated at 35° C. (the bath temperature) under reduced pressure
  2. customto furnish a fluorescent product which
  3. customwas purified again with HPLC

Sources & evidence

ORD record
ord-4a97196d4eba463ca5fe9ee6924c5d9e
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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