Formic Acid → HCID 67001766, compound

HRID 2279228Notes

Reaction equation

HRID 2279228 reaction equation
C(O)=O.[CH2:4]([N:11]1[CH2:25][CH2:24][N:14]2[C:15]3[N:23]=[CH:22][CH:21]=[CH:20][C:16]=3[NH:17][CH2:18][CH2:19][CH:13]2[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:26]=O>C(Cl)Cl>[CH2:4]([N:11]1[CH2:25][CH2:24][N:14]2[C:15]3[N:23]=[CH:22][CH:21]=[CH:20][C:16]=3[N:17]([CH3:26])[CH2:18][CH2:19][CH:13]2[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 54670219HCID 54670219, compound

Product 1

HCID 67001766HCID 67001766, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

Formic acid (88%, 3 mL) was added to a solution of the product of Example 52 (97 mg, 0.231 mmol) in CH2Cl2 (2 mL). Aqueous formalin (0.5 mL, 6.5 mmol) was added, and the mixture was heated at 110° C. for 45 minutes, then cooled to room temperature and concentrated under vacuum. The residue was purified by HPLC (30×100 mm XBridge™ column cluting with aqueous 0.1 M (NH4)2CO3-methanol, 80:20-0:100 over 15 minutes) to provide the title compound: 1H NMR (300 MHz, CD3OD) δ ppm 1.62-1.74 (m, 1H), 1.77-1.91 (m, 1H), 2.23 (t, J=10.5 Hz, 1H), 2.39 (td, J=11.0, 3.1 Hz, 1H), 2.70 (ddd, J=10.8, 2.4, 1.9 Hz, 1H), 2.79 (s, 3H), 2.80-2.88 (m, 1H), 2.96 (ddd, J=11.1, 6.5, 4.4 Hz, 1H), 3.23-3.29 (m, 1H), 3.32-3.40 (m, 2H), 3.50 (dt, J=12.9, 3.1 Hz, 1H), 3.59 (s, 2H), 6.87 (dd, J=7.8, 4.7 Hz, 1H), 7.08 (dd, J=7.8, 1.4 Hz, 1H), 7.22-7.39 (m, 5H), 7.71 (dd, J=4.9, 1.5 Hz, 1H); MS (ESI) m/z 309 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by HPLC (30×100 mm XBridge™ column cluting with aqueous 0.1 M (NH4)2CO3-methanol, 80:20-0:100 over 15 minutes)

Sources & evidence

ORD record
ord-ca095b1581174d95946b483d63e870b2
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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