Hydrochloric Acid → HCID 59511452, compound

HRID 1157791Notes

Reaction equation

HRID 1157791 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[C:5]2[NH:28][CH:29]=[C:30]([C:31](=[O:51])[C:32](=[O:50])[N:33]3[CH2:38][CH2:37][N:36]([C:39]4[N:43]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=5)[N:42]=[N:41][N:40]=4)[CH2:35][CH2:34]3)[C:4]=12.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)=[CH:11][CH:10]=2)=[C:5]2[NH:28][CH:29]=[C:30]([C:31](=[O:51])[C:32]([N:33]3[CH2:38][CH2:37][N:36]([C:39]4[N:43]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=5)[N:42]=[N:41][N:40]=4)[CH2:35][CH2:34]3)=[O:50])[C:4]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59511482HCID 59511482, compound

Product 1

HCID 59511452HCID 59511452, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 4-(4-(4-methoxy-3-(2-oxo-2-(4-(1-(pyridin-2-yl)-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)phenyl)piperazine-1-carboxylate (250 mg, 0.360 mmol) in 1,4-dioxane (2 mL) was added 4N HCl in 1,4-dioxane (0.450 mL, 1.802 mmol) at room temperature, the mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure. The resulting crude was purified by prep HPLC to give 1-(4-methoxy-7-(4-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-(pyridin-2-yl)-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (200 mg, 93%) as white solid. LCMS: m/e 594.55 (M+H)+, ret time 1.76 min (method 4). 1H NMR (500 MHz, MeOD) δ ppm 3.42-3.48 (m, 4H) 3.50 (m, 2H) 3.54 (m, 2H) 3.64-3.70 (m, 4H) 3.71 (m, 2H) 3.90 (m, 2H) 4.16 (s, 3H) 7.36 (d, J=8.54 Hz, 2H) 7.63 (dd, J=7.17, 5.04 Hz, 1H) 7.82 (d, J=8.85 Hz, 2H) 7.90 (d, J=8.24 Hz, 1H) 8.04 (s, 1H) 8.17 (t, J=7.63 Hz, 1H) 8.63-8.75 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting crude was purified by prep HPLC

Sources & evidence

ORD record
ord-3474d44757bd4588b37839bfeb7e1287
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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