Formic Acid → HCID 66746870, compound

HRID 711719Notes

Reaction equation

HRID 711719 reaction equation
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].C(O)=O.[NH2:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:13]=1[C:14]#[N:15].CCN(CC)CC>C(Cl)Cl>[S:2]([NH:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[C:13]=1[C:14]#[N:15])(=[O:4])(=[O:3])[NH2:5]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 67398866HCID 67398866, compound

Product 1

HCID 66746870HCID 66746870, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of chlorosulfonyl isocyanate (212 mg, 1.50 mmol) in CH2Cl2 (0.55 mL) at 0° C., was added formic acid (0.575 mL) under N2. The reaction was stirred for 30 min, and a solution of 2-amino-6-(4-methoxybenzyloxy)benzonitrile (Example 114b) (191 mg, 0.75 mmol) in CH2Cl2 (4 mL) was added at 0° C., followed by Et3N (0.627 mL, 4.50 mmol). After 30 min, the reaction was concentrated in vacuo and diluted with water. The pH was adjusted to 7 with concentrated HCl, and purified by reverse phase HPLC (10-90% acetonitrile in water) to provide 2-sulfamoylamino-6-(4-methoxybenzyloxy)benzonitrile (130 mg, 52%). 1H NMR (400 MHz, MeOD) δ 3.80 (s, 3H), 5.15 (s, 2H), 6.88 (d, J=8.1 Hz 1H), 6.94 (m, 2H), 7.40 (m, 2H), 7.48 (t, J=8.7 Hz, 1H), 7.75 (dd, J=8.6, 0.8 Hz, 1H).

Workup

  1. waitAfter 30 min
  2. concentrationthe reaction was concentrated in vacuo
  3. additiondiluted with water
  4. custompurified by reverse phase HPLC (10-90% acetonitrile in water)

Sources & evidence

ORD record
ord-7f2352ac0caf431695f7737d09a510c3
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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