Ammonia → HCID 9847665, compound

HRID 1767183Notes

Reaction equation

HRID 1767183 reaction equation
ClC1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH:19]=1)[C:16](O)=[O:17])[CH:6]=[C:5]2[C:20]1[C:21](=[O:34])[NH:22][C:23](=[O:33])[C:24]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32].C1C=CC2N(O)N=[N:41]C=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.N.[CH2:61]([Cl:63])Cl>CN(C=O)C>[Cl:63][C:61]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH:19]=1)[C:16]([NH2:41])=[O:17])[CH:6]=[C:5]2[C:20]1[C:21](=[O:34])[NH:22][C:23](=[O:33])[C:24]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 21113485HCID 21113485, compound

Product 1

HCID 9847665HCID 9847665, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of Compound 56 (80 mg, 0.17 mmol) in DCM (2 mL) and DMF (0.5 mL) was added HOBT (25.7 mg, 0.19 mmol) and DCC (37 mg, 0.18 mmol). The reaction was stirred at room temperature for 30 min, then 28% aqueous NH3 (15 mg, 0.36 mmol) was added. The reaction stirred at room temperature overnight. The reaction mixture was filtered and the filtered solid was washed with DCM (2 mL). The filtrate was diluted with ethyl acetate (6 mL), washed twice with NaHCO3 (2 mL), dried (Na2SO4) and evaporated in vacuo. The crude product was purified via flash column chromatography (DCM:MeOH:NH4OH 93:5:2) to give Compound 58 (36.7 mg, 46%). Compound 58 was dissolved in methanol and treated with 1N HCl/CH3CN (2:1) and lyophilized to give the HCl salt. 1HNMR (DMSO-d6) δ 11.2 (s, 1H), 9.11 (s, 1H), 9.03 (s, 1H), 8.45 (s, 1H), 8.32 (d, J=12.0, 2H), 7.80 (s, 1H), 7.58–7.47 (m, 3H), 7.34–7.01 (m, 3H), 6.42 (s, 1H), 3.34 (s, 3H). ES-MS m/z 473 (MH+).

Workup

  1. stirringThe reaction stirred at room temperature overnight
  2. filtrationThe reaction mixture was filtered
  3. washthe filtered solid was washed with DCM (2 mL)
  4. additionThe filtrate was diluted with ethyl acetate (6 mL)
  5. washwashed twice with NaHCO3 (2 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe crude product was purified via flash column chromatography (DCM:MeOH:NH4OH 93:5:2)

Sources & evidence

ORD record
ord-50d1ebac30ae459dbb7390d448e00651
Source dataset
uspto-grants-2007_06
Patent number
US07232906B2

Reaction notes

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