Water → HCID 68461384, compound

HRID 2197939Notes

Reaction equation

HRID 2197939 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15]C(=O)C)=[C:4]([NH:19][C:20]2[C:29]3[C:24](=[N:25][C:26]([CH2:30][CH2:31][CH3:32])=[CH:27][CH:28]=3)[N:23]=[CH:22][CH:21]=2)[CH:3]=1.O.[OH-].[Na+]>Cl>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[NH:19][C:20]1[C:29]2[C:24](=[N:25][C:26]([CH2:30][CH2:31][CH3:32])=[CH:27][CH:28]=2)[N:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68458395HCID 68458395, compound

Product 1

HCID 68461384HCID 68461384, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The product from Example 185d was dissolved in 50% HCl:H2O and heated to 100° C. for 1 hr. Reaction mixture was then cooled to room temperature, made basic with 2N NaOH, and extracted with CH2Cl2. Dried over Na2SO4, filtered and concentrated under vacuum giving the crude title compound. Purified by HPLC with TFA providing the product as a trifluoroacetic acid (87 mg, 64%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.35 Hz, 3H), 1.79-1.92 (m, J=7.43, 7.43, 7.43, 7.43, 7.43 Hz, 2H), 2.32 (s, 3H), 3.00 (t, J=7.54 Hz, 2H), 6.34 (d, J=6.99 Hz, 1H), 6.49 (t, J=7.54 Hz, 1H), 6.68 (d, J=6.99 Hz, 1H), 6.92 (d, J=8.09 Hz, 1H), 7.05-7.13 (m, 1H), 7.15-7.20 (m, 1H), 7.24 (d, J=8.46 Hz, 1H), 7.28 (s, 1H), 7.84 (d, J=8.82 Hz, 1H), 8.42 (d, J=6.99 Hz, 1H), 9.06 (d, J=8.82 Hz, 1H); MS (ESI+) m/z 401 (M+H−TFA)+; (ESI−) m/z 399 (M−H−TFA)−.

Workup

  1. customReaction mixture
  2. extractionextracted with CH2Cl2
  3. dry with materialDried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-726d28cdf32a4ec3a3f2ad3920e65812
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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