Hydrochloric Acid → HCID 58298740, compound

HRID 1771869Notes

Reaction equation

HRID 1771869 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([NH:13][C:14]3[CH:19]=[C:18]([NH:20][C:21](=[O:42])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29]5[C:30]6[CH:38]=[CH:37][C:36]([CH:39]([CH3:41])[CH3:40])=[N:35][C:31]=6[N:32]=[CH:33][N:34]=5)[CH:23]=4)[CH:17]=[CH:16][C:15]=3[S:43][C:44]3[CH:49]=[CH:48][C:47]([NH:50]C(=O)OC(C)(C)C)=[CH:46][CH:45]=3)=[N:11][CH:10]=[N:9][C:8]=2[N:58]=1)([CH3:3])[CH3:2].Cl>O1CCOCC1>[NH2:50][C:47]1[CH:48]=[CH:49][C:44]([S:43][C:15]2[CH:16]=[CH:17][C:18]([NH:20][C:21](=[O:42])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29]4[C:30]5[CH:38]=[CH:37][C:36]([CH:39]([CH3:41])[CH3:40])=[N:35][C:31]=5[N:32]=[CH:33][N:34]=4)[CH:23]=3)=[CH:19][C:14]=2[NH:13][C:12]2[C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[N:58][C:8]=3[N:9]=[CH:10][N:11]=2)=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59376879HCID 59376879, compound

Product 1

HCID 58298740HCID 58298740, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The product from Example 7C (40 mg, 0.050 mmol) was dissolved in dioxane (2.0 mL) and 4M HCl in dioxane (0.25 mL) was added. This solution was stirred at room temperature overnight. The solid HCl salt of the product was filtered off then dissolved in methanol and added to saturated NaHCO3. Extracted with ethyl acetate and evaporated. Purification by chromatography on silica gel eluting with (0% to 30% methanol in dichloromethane) gave the title compound (13 mg, 37% yield). 1H NMR (300 MHz, DMSO-D6) d ppm 1.36 (dd, J=6.80, 4.23 Hz, 12H) 3.20-3.30 (m, 2H) 6.57 (d, J=8.46 Hz, 2H) 7.04-7.12 (m, 3H) 7.60-7.70 (m, 2H) 7.82-7.95 (m, 3H) 8.00-8.08 (m, 2H) 8.29 (s, 1H) 8.83-8.93 (m, 2H) 9.09 (d, J=12.50 Hz, 1H) 9.17 (d, J=7.72 Hz, 1H) 10.58 (s, 1H) 11.38 (s, 1H) 11.69 (s, 1H). MS (ESI) m/z 693 (M+H)+.

Workup

  1. filtrationThe solid HCl salt of the product was filtered off
  2. dissolutionthen dissolved in methanol
  3. additionadded to saturated NaHCO3
  4. extractionExtracted with ethyl acetate
  5. customevaporated
  6. customPurification by chromatography on silica gel eluting with (0% to 30% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4f1f4ff222b046e7a0769753ffa04d40
Source dataset
uspto-grants-2016_02
Patent number
US09249138B2

Reaction notes

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