3-Aminobenzoic Acid → HCID 136347357, compound

HRID 601356Notes

Reaction equation

HRID 601356 reaction equation
[NH2:1][C:2]1[C:11]2[S:10](=[O:13])(=[O:12])[N:9]=[C:8]([C:14]3[C:15](=[O:30])[N:16]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]4[C:22]([C:23]=3[OH:24])=[CH:21][CH:20]=[CH:19][CH:18]=4)[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:31].[NH2:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=1)[C:36](O)=O>>[NH2:32][C:33]1[CH:34]=[C:35]([C:36]2[O:31][C:3]3[CH:4]=[CH:5][C:6]4[NH:7][C:8]([C:14]5[C:15](=[O:30])[N:16]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]6[C:22]([C:23]=5[OH:24])=[CH:21][CH:20]=[CH:19][CH:18]=6)=[N:9][S:10](=[O:12])(=[O:13])[C:11]=4[C:2]=3[N:1]=2)[CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 136358419HCID 136358419, compound

Product 1

HCID 136347357HCID 136347357, compoundYield 38%

Conditions

Temperature
190 °C

Procedure

A mixture of the product of Example 354 (38 mg, 0.086 mmol) and 3-aminobenzoic acid (13 mg, 0.094 mmol) in polyphosphoric acid (1 mL)was heated to 190° C. for 1 hour. The solution was cooled to 25° C., triturated with water and a 10% solution of sodium carbonate. The solid was filtered, dried, and purified by flash column, eluting with 2% methanol in dichloromethane to yield the title compound (15 mg, 38%). The sodium salt was made by the procedure of Example 1D. MS (ESI−) m/z 543 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ 1.04 (d, J=6.62 Hz, 6 H) 1.86 (m, 1 H) 2.56 (m, 2 H) 5.53 (s, 2 H) 5.96 (t, J=7.35 Hz, 1 H) 6.82 (ddd, J=8.09, 2.21, 1.10 Hz, 1 H) 7.08 (td, J=7.35, 1.47 Hz, 1 H) 7.27 (m, 2 H) 7.36 (dt, J=7.72, 1.29 Hz, 1 H) 7.57 (m, 3 H) 7.96 (d, J=8.82 Hz, 1 H) 8.10 (dd, J=8.09, 1.47 Hz, 1 H) 16.51 (s, 1 H).

Workup

  1. temperatureThe solution was cooled to 25° C.
  2. customtriturated with water
  3. filtrationThe solid was filtered
  4. customdried
  5. custompurified by flash column
  6. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-a8d86163c40742d1a2b52d1d2f130f02
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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