Cyanoacetic acid → HCID 178456264, compound

HRID 1943473Notes

Reaction equation

HRID 1943473 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:28][C:29]3[CH:33]=[CH:32][N:31]([CH:34]([CH3:36])[CH3:35])[N:30]=3)[C:12]3[N:13]([C:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][C:22]=4[F:27])=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1.[C:37]([CH2:39][C:40](O)=[O:41])#[N:38].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[C:37]([CH2:39][C:40]([NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:28][C:29]3[CH:33]=[CH:32][N:31]([CH:34]([CH3:36])[CH3:35])[N:30]=3)[C:12]3[N:13]([C:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][C:22]=4[F:27])=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1)=[O:41])#[N:38]

Participants

6

Reactant 4

HCID 9740Cyanoacetic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178456263HCID 178456263, compound

Product 1

HCID 178456264HCID 178456264, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of Example 48 and 2-cyanoacetic acid (4.01 mg, 0.047 mmol) in DCM (1 mL) was added DIEA (0.035 mL, 0.200 mmol) and BOP (20.87 mg, 0.047 mmol). The mixture was stirred at room temperature for 30 minutes and then concentrated. The crude reaction mixture was purified by reversed-phase preparative HPLC to give the title compound (8.1 mg, 61%) as white solid. HPLC Rt=2.981 min (Chromolith SpeedROD 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min gradient, monitored at 220 nm), [M+H]=560.

Workup

  1. concentrationconcentrated
  2. customThe crude reaction mixture
  3. customwas purified by reversed-phase preparative HPLC

Sources & evidence

ORD record
ord-03a24d07bfab4720a55dbccc4ae2101d
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

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