Hydrochloric Acid → HCID 58300043, compound

HRID 79136Notes

Reaction equation

HRID 79136 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24]3[N:25]=[CH:26][C:27]4[C:32]5[CH:33]=[CH:34][N:35]=[C:36]([Cl:37])[C:31]=5[N:30]([CH:38]5[CH2:42][CH2:41][CH2:40][CH2:39]5)[C:28]=4[N:29]=3)=[N:21][CH:22]=2)[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.Cl>CO>[Cl:37][C:36]1[C:31]2[N:30]([CH:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[C:28]3[N:29]=[C:24]([NH:23][C:20]4[N:21]=[CH:22][C:17]([N:14]5[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][OH:8])[CH2:12][CH2:13]5)=[CH:18][CH:19]=4)[N:25]=[CH:26][C:27]=3[C:32]=2[CH:33]=[CH:34][N:35]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58300162HCID 58300162, compound

Product 1

HCID 58300043HCID 58300043, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Compound 217 (0.094 g, 0.15 mmol) was combined with 10 mL of methanol and 4 mL of 1N HCl. The solution was stirred at room temperature overnight. The solution was concentrated under vacuum and the residue obtained was purified on CombiFlash column (dry loaded), eluting with a gradient of 2% methanol/0.1% NH4OH (˜28% in water)/DCM to 10% methanol/0.5% NH4OH (˜28% in water)/DCM. The fractions containing the product were combined and concentrated under vacuum to give a yellow solid. The solid was partially dissolved in methanol and then collected on filter paper. Washed the solid off of the filter paper with DCM/methanol through a fritted funnel and then concentrated under vacuum to give compound 213 (0.065 g, 85% yield) as a yellow solid. 1H-NMR (500 MHz, DMSO-d6) δ 9.92 (1 H, s), 9.33 (1 H, s), 8.22 (1 H, d, J=5.1 Hz), 8.10 (1 H, d, J=4.9 Hz), 8.04 (1 H, d, J=2.9 Hz), 8.02 (1 H, d, J=9.0 Hz), 7.46 (1 H, dd, J=9.0, 2.9 Hz), 5.95-6.05 (1 H, m), 4.43 (1 H, t, J=5.4 Hz), 3.54 (2 H, q, J=6.1 Hz), 3.12-3.19 (4 H, m), 2.55-2.65 (6 H, m), 2.45 (2 H, t, J=6.4 Hz), 1.98-2.08 (4 H, m), 1.65-1.75 (2 H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 493.1.

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customthe residue obtained
  3. customwas purified on CombiFlash column (dry loaded)
  4. washeluting with a gradient of 2% methanol/0.1% NH4OH (˜28% in water)/DCM to 10% methanol/0.5% NH4OH (˜28% in water)/DCM
  5. additionThe fractions containing the product
  6. concentrationconcentrated under vacuum
  7. customto give a yellow solid
  8. customcollected
  9. filtrationon filter paper
  10. washWashed the solid off of the filter paper with DCM/methanol through a fritted funnel
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5b35842b7d204b4b90e1941c03aa7a0f
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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