Ammonia → HCID 60054756, compound

HRID 489247Notes

Reaction equation

HRID 489247 reaction equation
ClC(OCC(C)C)=O.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[C@:21]3([N:25]([CH3:26])[C:24](=[O:27])[N:23]([C:28]4[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=4)[C:22]3=[O:36])[CH2:20][N:19]([CH2:37][C:38](O)=[O:39])[CH2:18]2)=[CH:13][CH:12]=1)#[N:10].C[N:42]1CCOCC1.N>C(Cl)Cl.O>[C:9]([C:11]1[CH:12]=[CH:13][C:14]([C@H:17]2[C@:21]3([N:25]([CH3:26])[C:24](=[O:27])[N:23]([C:28]4[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=4)[C:22]3=[O:36])[CH2:20][N:19]([CH2:37][C:38]([NH2:42])=[O:39])[CH2:18]2)=[CH:15][CH:16]=1)#[N:10]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 60054676HCID 60054676, compound

Product 1

HCID 60054756HCID 60054756, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Isobutyl chloroformate (27 μl, 0.21 mmol) was added to a cooled (5° C.) suspension of Example 64 (90 mg, 0.19 mmol) and N-methyl morpholine (23 μl, 0.2 mmol) in DCM (4 ml). After 1 h, ammonia (420 μl, 0.5 M in dioxane, 0.21 mmol) was added. After 1 h at 5° C. and 3 h at RT, water (2 ml) was added. The organic layer was separated and the aqueous layer extracted with DCM. The combined organic layers were concentrated in vacuo and the resulting material was purified by chromatography over silica gel (eluent: DCM/MeOH 95/5) to yield the above-titled compound as a solid (49.6 mg). 1H NMR (CDCl3): 7.64 (2H, d, J=8.2 Hz), 7.25-7.30 (3H, m), 6.84 (1H, br s), 6.65 (2H, d, J=1.5 Hz), 6.18 (1H, br s), 3.87 (1H, t), 3.4-3.5 (5H, m), 3.24 (3H, s), 3.15 (1 H, d, J=10.9 Hz).

Workup

  1. waitAfter 1 h at 5° C.
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with DCM
  4. concentrationThe combined organic layers were concentrated in vacuo
  5. customthe resulting material was purified by chromatography over silica gel (eluent: DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-7d0cab4e25874b0e809e32184a7c0e97
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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