Sodium Bicarbonate → HCID 178428293, compound

HRID 1503843Notes

Reaction equation

HRID 1503843 reaction equation
[C:1]([C:3]1[C:4]2[N:41](COCC[Si](C)(C)C)[CH:40]=[N:39][C:5]=2[C:6]([CH2:30][C:31]2[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:38])=[N:7][C:8]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)=[C:12]([CH3:29])[CH:11]=1)#[N:2].C(=O)(O)[O-:51].[Na+]>S(=O)(=O)(O)O.O>[Cl:37][C:36]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:38])[C:31]=1[CH2:30][C:6]1[C:5]2[N:39]=[CH:40][NH:41][C:4]=2[C:3]([C:1]([NH2:2])=[O:51])=[C:8]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)=[C:12]([CH3:29])[CH:11]=2)[N:7]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86725395HCID 86725395, compound

Product 1

HCID 178428293HCID 178428293, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of the product of Example 29A (120 mg, 0.17 mmol) in concentrated sulfuric acid (5 mL) was added water (1 mL) at 0° C. and the mixture was heated at 95° C. for 20 minutes. After cooling to ambient temperature, the mixture was diluted with water (3 mL), and the pH was adjusted to pH 8-9 with saturated sodium bicarbonate solution. The mixture was extracted with dichloromethane (3×20 mL). The combined organic phase was concentrated and the residue was purified via preparative HPLC using a gradient of 10/90 to 80/20 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 3 00 MHz): δ 13.55 (br, 1H), 11.66 (s, 1 H), 9.58 (s, 1 H), 8.67 (s, 1 H), 8.57 (s, 1 H), 7.81 (s, 1 H), 7.57-7.54 (m, 1 H), 7.41-7.36 (m, 1 H), 7.11 (dd, J=8.4, 2.1 Hz, 1 H), 7.05 (d, J=2.1 Hz, 1 H), 6.62 (d, J=8.4 Hz, 1 H), 4.69 (s, 2H), 3.23-3.22 (m, 4 H), 2.94-2.92 (m, 4 H), 2.14 (s, 3 H). MS: 510 (M+H+).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionThe mixture was extracted with dichloromethane (3×20 mL)
  3. concentrationThe combined organic phase was concentrated
  4. customthe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-e214dac5e82243d2981930b2a0d34971
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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