Ammonium Chloride → HCID 44158491, compound

HRID 1926359Notes

Reaction equation

HRID 1926359 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([OH:22])=O)[CH2:15][CH2:14]3)[CH:12]=2)=[CH:4][C:3]=1[C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1.[NH4+].[Cl-].C[N:35](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH:13]3[CH2:14][CH2:15][N:16]([CH2:19][C:20]([NH2:35])=[O:22])[CH2:17][CH2:18]3)[CH:12]=2)=[CH:4][C:3]=1[C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 44158490HCID 44158490, compound

Product 1

HCID 44158491HCID 44158491, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of {4-[4-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-piperidin-1-yl}-acetic acid (10.0 mg, 0.0184 mmol), NH4Cl (2.0 mg, 0.037 mmol), TBTU (8.86 mg, 0.0276 mmol) and DMF (1 mL) was charged with DIPEA (0.03 mL, 0.2 mmol) and allowed to stir at rt for 10 min. The solution was used directly for HPLC purification. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=2.17-2.35 (m, 4H), 2.69 (td, J=11.9, 2.5 Hz, 2H), 3.28 (d, J=12.4 Hz, 2H), 3.37 (s, 2H), 4.29-4.40 (m, 1H), 7.41-7.47 (m, 1H), 7.53 (td, J=7.6, 1.3 Hz, 1H), 7.89 (s, 1H), 8.01 (dd, J=12.3, 8.0 Hz, 2H), 8.11 (s, 1H), 8.19 (d, J=2.0 Hz, 1H), 8.32 (d, J=2.3 Hz, 1H).

Workup

  1. customThe solution was used directly for HPLC purification
  2. additionThe fractions containing the pure product
  3. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-25a3c52ff87a4439ab44825e993126c2
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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